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Like creating a successful business, it's not so much about following a "do these 5 things" article. It's more about solving hard problems that take time, discipline, and thoughtfulness.

I recently read an outstanding book that I can't recommend enough. It focuses on this very topic. It's called "Finish Big". Here's a link to it on amazon.

In short, the author's general philosophy is to create a healthier, better running business for yourself, because that will ultimately increase the value of the business in the eyes of a purchaser. Namely:

• Reduce the businesses dependency upon you
  
• Obvious basics: have a high margin and show good growth
  
• Make the business more durable to market changes
  
• Learn to appreciate how long the sale process actually takes
  
• Learn to appreciate how you really need help during a sale process as everyone involved in it has different motivations than you do and you probably have the least experience of all of them.
  
  Read this book. You will thank yourself and it'll receive a permanent place on the bookshelf!

First, I want to say, welcome to the wonderful world of real estate. You have a LOT to learn and it takes time. Don't let that discourage you.


Second, anyone financially sophisticated would never put their money in residential for a number of obvious reasons. My guess would be you have only ever bought a house, so that is where you are comfortable. I won't even get into how incredibly inefficient and what a poor investment residential is, particularly trying to buy 400-500 homes. There is a whole list of books you would need to read, just to have a discussion on the topic. To be fair, I will recommend one book you should read immediately ( https://www.amazon.com/gp/product/0471684058/ref=ppx_yo_dt_b_search_asin_image?ie=UTF8&psc=1). I picked this one specifically for you because he actually compares residential to commercial in it.


Third, you would never approach a real estate broker (very strange recommendation by LordAshon). Brokers don't own property's, they get a commission for closing them. Many commercials brokers have no idea what they are doing. The good ones are exceptions and not the rule. 50% of all commercial deals are done without brokers. You don't bring brokers into the deal unless you are ready to make an offer (and they have the listing) or are sending your specific requirements for purchasing. Truthfully though, if you were going to move forward with some sort of portfolio (like hundreds of homes)...you would need an attorney, not a broker.


Fourth, You should find someone who actually has experience in analyzing, making offers, doing due diligence and closing multi-million dollar deals. There is a reason why capital groups have teams of people involved.


What you should be doing, is looking into are capital groups, rather than funds to invest with. Don't lose your friends and associate's money. I can already tell you are going to make a LOT of mistakes that will cost millions. Please don't do that! They won't be friends for long if you lose their capital.

1. What are the actual goals for the group and its members? Tax deduction? Income? Portfolio diversification? Inflation protection/hedge?
   
   Each of these questions has a different answer and strategy related to it. You should group these people together so that interest is aligned in that particular investment.
   
   
2. Where are the funds from each member coming from? Some may use tax-sheltered accounts and others may not.
   
   You need to adjust the strategy to reflect this. For example, if someone is using a self-directed Roth IRA, they can not be invested in any property with a mortgage/lien because the investment is still subject to UBIT tax and negates the whole point of the ROTH.
   
   
   
3. How do you plan to structure the company? LLC's, Trusts? A combination? Some more advanced structures I won't mention (which is where you probably should be)?
   
   
   With the right capital group, you should be able to double your money nearly every 5 years or so (but you have to buy right, to hit these numbers). With $10 million, you should be able to leverage roughly $35-$40 million in assets. In 5 years, that $10 million should grow to $20-30 million. Partnering with a capital group would be the best way to learn the business or just let them do all the hard work for you (do you really want a full-time job?). Finding the right fit could take a year. I can make a couple of recommendations if I knew what your financial goals were.
   
   
   A couple of things to consider, if you don't use leverage and you get sued, you can lose 100% of your equity in that LLC. Leverage is actually quite an important strategy. You need to understand your tax implications to the partners and this should be known before you ever make any offers.
   
   
   As far as markets go (I won't tell you how you future proof your investments using demographics, this is something that should be earned): What I will tell you is all the movement is heading south. 10,700 people retire per day...this will continue until 2023. Millennials are relocating south because that is where the job growth is. Parts of Arizona, Atlanta metro, other areas outside of Dallas/Fort Worth in Texas, almost all of the Florida coastline.

>Maybe it’s networth that makes you feel better and not necessarily the income?

Think of it like this, who is truly wealthier in this scenario the person making $60k\year and saving $15K after taxes or the person making $200k\year and only saving $5k?

I would suggest you read "the millionaire next door" by Thomas Stanley it changed my entire outlook on money. https://www.amazon.com/Millionaire-Next-Door-Surprising-Americas/dp/1589795474

It seems like you have a lot of expenses right now and at your income level you should be able to easily cut back in certain area's in order to save over a million dollars in a few short years which will probably help to alleviate those feelings of "not feeling rich." If I was at that income level I would be living like I only made $75K\year and saving the rest and within 10 years would probably never have to work again. It seems lifestyle creep is what significantly delays building true wealth and could delay your retirement.

Two more thoughts:

a. Leverage

b. Work hours

Leverage:

I am going to submit that the single largest lever you have on your financial wealth is the ability to negotiate, and the first principle of negotiation is understanding your leverage. I missed on first reading that you think that you can use this outside job opportunity to leverage your current job salary.

On the path to FATfire, I think this is incredibly important.

If I were you, my first principle would be to run the play of using this to get your salary up at your current job. This is a "must learn" experience. However, the second key of negotiation is always be willing to take the alternative path. From your posting, the alternative isn't all that bad.

If you want to understand how you get a raise in salary without burning bridges, you can PM me. However, the simple principle is:

a. You find an internal coach and "confess" the higher offer. This is not always your manager, but ideally it should be.

b. Say that you really don't want to go, but you don't see how you can turn down the offer.

c. Indicate that the new place is "really more expensive" because I don't think that if you set exceptions to double your salary will be acceptable. (Although I have personally had my salary doubled in this type situation.)

By the way, people have always sought me out as a career coach, and I have a couple of people I am mentoring now. The success rate on this is about 80%, and in today's environment, it never burns a bridge unless you have a psychotic boss or there is a strict policy on not countering, which is very rare, and you seem to indicate you might see a counter. (And you get one of these every 5 years. If you do this twice in quick succession, you'll be shown the door.)

If they don't counter, and you sound reasonable, you probably need to move. They don't appreciate you.

I consider salary negotiation a critical life skill, and I think you have to exercise this option. But again, this is your life choice, and I'm just brainstorming.

Next subject: Let's talk about hours:

1. All moguls work 70 to 100 hours.
   
2. Therefore I need to work 70 to 100 hours.
   
   If you read the literature, you will find out that most people simply are not efficient at 70 hours per week. A nice survey of the research be understood by reading this book, although it is a bit dated. The issue is that these mogul are genetically wired to work these high hours. [Often they have high degrees of conscientiousness, extraversion, and often neuroticism as measured on the big five personality test.]
   (https://en.wikipedia.org/wiki/Big_Five_personality_traits)
   
   I think the literature overwhelming argues these are hardwired, so you are or you aren't this way. Then again, I am a Steven Pinker fan.
   
   We see this often with engineers on a big push to finish a project, and we push the general population beyond 55 hours per week (the limit for what I think is reasonable for this class of individuals), and they start to create more bugs than forward progress. The solution was more hours, but we actually go backwards. Mind you, I want to continue to state that their are some individual that strive on high hours. Normally, you never ask them to work that much. They can't help it.
   
   The problem is that some companies and cultures make 70 hours a week a "requirement." The financial industry, residency at hospitals, and Japan come to mind. I am familiar with two of these three (hospitals/Japan), and I believe I can make a convincing argument for why their high work culture creates as many problems as it solves, but this goes beyond a post in a forum.
   
   So what happens when a "standard" person gets thrown into a high hour environment?
   
   a. They play the game. They stay at work for 70 hours, but they take a lot of meetings, goof off when nobody's looking, and suck up to the boss to play the political game. 80-90% percent of companies, this happens.
   
   b. They push to 70 hours in real work and try to get real work done, and get burnt to a crisp. A lot of people basically say "I hate my job, I'm getting out." You basically redline your car's engine, and screw up the engine block.
   
   Again, these are personal opinions from somebody in their late 50s that can FATfire with $7-8M, and there are folks that are better off than me here.
   
   However, most of these principles really came from my Dad, who FATfired with about $7-8m (today's dollars) at 62. (My wealth is separate from his, so my actual number is closer to $12M--but a big chunk is not liquid). We both went up corporate America, assign a massive amount of our good fortune to God's providence, but we also believe that there are some principles that everybody can apply.

>>The jets and all that other crap seem like a better value renting.
>
>Huh? $3 million in total wealth isn't much, especially for that. Please, don't do that. I strongly recommend that you read The Millionaire Next Door: The Surprising Secrets of America's Wealthy.

Yeah, that bit made me laugh. $3m isn't even remotely close to private jet territory. Try $300m. Lol

Most people that receive a large windfall like this do not fare well OP. At all. Be extremely careful with this money and do not tell anybody. Check out the "Windfall" section in the /r/personalfinance wiki. Also check out /r/fire and /r/fatFIRE.

>The jets and all that other crap seem like a better value renting.

Huh? $3 million in total wealth isn't much, especially for that. Please, don't do that. I strongly recommend that you read The Millionaire Next Door: The Surprising Secrets of America's Wealthy. I know several that make that amount in less than 2 months, and you wouldn't know it, because they live frugally and humbly, including driving beat-up old minivans. Some of them do have nice shit (e.g. palace-sized mansions) but out in the street, they don't flex, and others live in small, modest homes in middle class neighborhoods. At best, they might have a Model 3, S, or X that they also use.

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For the sake of argument and with some fuzzy math, if you put all $3 million into an index fund that's earning you 6%, that's $180,000/year. That is a lot of money for a 20 year old, and an obligatory Uncle Ben quote goes here. You're virtually set for life and can do anything that you want, and I'd probably use that time and money to go become a full time student in any number of mediums: Udacity, College, Trade School, Real Estate, etc. which would further your skill level for other interests, including but not limited to said rental houses. If you got licensed in trades, you'd be able to legally (well, from a liability angle - nothing is really stopping you from your own maintenance anyways) do your own repair work on your properties, which would save you even more money. I'm not saying that's the most logical option, but it's something to bear in mind.

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To answer the relationship/cash aspect (and because I got f'd on this) you'd want a pre-nup, and as others have advised, a great attorney. Some of the relationship warning signs that I wish that I had known, and was covered in this forum yesterday. When it comes to getting serious about a relationship (and until then, if you're going to be active, use protection - child support and/or divorce rape should be a part of your threat vector) then you might want to ask an attorney about shifting assets around to where you're then an employee of yourself (e.g. form an LLC, hire yourself, and pay a meager wage, with the option for bonuses.)

First, keep enough in your passive funds to keep you going even if you lose the rest. Pull out your SWR and that's it, no matter what. Then maybe keep another chunk passive that you only move to active after you've had some success with that.

For the active funds, it depends what you're interested in. If you want to contribute to society while making money, another option is angel investing. Look for small startups that need early funding, and have some potential for making a positive impact.

There are some books on Amazon that look decent; I've read part of this one and it sounds like a lot of work, but potentially rewarding.

But don't go into it lightly. It's easy to throw your money away.

Try to keep in mind that popular media rarely presents a proportionately balanced view of the world. Due to fundamental incentives, media tends to be biased toward particular kinds of attention-grabbing sensationalism and pessimism.

Wanting to accurately perceive the state of the overall world beyond our personal experiences is admirable, so good for you. Investing the time to increase understanding helps us react rationally and responsibly.

A useful starting place is this brief TED talk by the amazing statistician Hans Rosling. Good books include Pinker's "Enlightenment Now: The Case for Reason, Science, Humanism, and Progress" and Ridley's "The Rational Optimist: How Prosperity Evolves".

VC here. Finally created an account to answer your question. Before doing anything, read these two books:

1. Angel by Jason Calacanis https://www.amazon.com/Angel-Invest-Technology-Startups-Timeless-Investor/dp/0062560700
   
   
2. Venture Deals by Brad Feld https://www.amazon.com/Venture-Deals-Smarter-Lawyer-Capitalist-ebook/dp/B01M3UIVW3/ref=mp_s_a_1_2?keywords=venture+deals+brad+feld&qid=1563846931&s=gateway&sprefix=venture+dea&sr=8-2
   
   The first book provides a high level overview of angel investing while the second goes into some of the nitty gritty details.
   
   From there, if you’re still interested, I’d recommend looking up your regional angel investor network. Pretty easily found on google. Most cities have them (Baltimore Angels, New Dominion Angels, etc...)Ask to come sit in on one or two of their pitch events. Get coffee with the other angels in the room and hear about their experiences.
   
   If you’re still interested, I’d join the group (all have some nominal fee) but you’ll get practice reps at analyzing companies, access to dealflow, and a good platform to start building a network. Other key takeaways:
   
   
3. Only allocate what you’re willing to lose (10% of NW is a rough estimate for alts depending on how big you are)
   
   
4. You need to be able to make 25+ bets. Often companies have minimum check sizes, so joining a group allows you to pool.
   
   
5. Invest in what you know.
   
   
6. Invest where you can help. (I.e. former F500 CISO angel investing in cyber security startups)

Do you or your spouse have the option of being paid as a contractor? If so, that suddenly allows you to expense many things such as a work vehicle, home office, meals, etc. You can find other threads on here discussing this.

As others have said, you might also interview other potential accountants. I didn’t realize how much variation there could be until I finally found a good one, and now it’s like night and day. I’d recommend reading What Your CPA Isn’t Telling You by Mark Kohler. It definitely opened my eyes to things I didn’t know were possible and gave me lots of good questions to ask when interviewing accountants.

I'd like to chime in and recommend you Stefan Zweig's biography of Montaigne. There's a beautiful description of Montaigne's childhood. He came from a similar family (financially secure), but reading how his father went about raising his son is very inspirational (on par with Gibran's 'On Children' in The Prophet). And don't worry, it's a short book, unlike the actual Essais.

Read this: How to Retire Happy, Wild, and Free: Retirement Wisdom That You Won't Get from Your Financial Advisor by Zelinski, Ernie J.

The Millionaire Mind is a book based on such a study you describe:

The Millionaire Mind targets a population of millionaires who have accumulated substantial wealth and live in ways that openly demonstrate their affluence. Exploring the ideas, beliefs, and behaviors that enabled these millionaires to build and maintain their fortunes, Dr. Stanley provides a fascinating look at who America's financial elite are and how they got there.

The Millionaire Mind https://www.amazon.com/dp/0740718584/ref=cm_sw_r_wa_apa_i_BY2LDbJYPQRD8

I’d recommend to OP, u/AnthonyNapoli, that they check out a book about this topic called: Uneasy Street: The Anxieties of Affluence.

The author interviewed people from households with a wide range of incomes ($100k to several million per year) and wide range of net worths (some around $10 million). What she found was that all refer to themselves as “middle class”.

It’s uncomfortable or maybe rude to think of oneself as poor or rich, so instead everyone says they are “middle class”. Middle class is considered the best class to be a part of.

Anyway that’s why it’s better to talk about percentiles, like income percentiles or net worth percentiles. That’s quantified and more concrete.

Just for a fun read I'll recommend you this book based on the life of a very famous stock speculator from the old days. He made and lost huge (like hundreds of millions of dollars in the 1920s) fortunes in his life. Just a great read.

https://www.amazon.com/Reminiscences-Stock-Operator-Marketplace-Book-ebook/dp/B00BOZBG2Q/

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Here's the wikipedia page on the actual guy:

https://en.wikipedia.org/wiki/Jesse_Lauriston_Livermore

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Spoiler alert:>! He ended up committing suicide in 1940. Beware market speculation, man!!<

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I liked this one:

https://www.amazon.com/All-About-Asset-Allocation-Second/dp/0071700781