Reddit mentions of The Essentials of Living Aboard a Boat

Where are you located? Location matters.

Recommend you read this book: https://www.amazon.com/Essentials-Living-Aboard-Revised-Updated/dp/0939837668

I live in Florida, but quite a few people migrate yearly and stay in good weather. Right now I haven't moved much with the boat because I have a land based job and spent the last 2 years getting out of debt and am now putting funds into the boat itself(solar panels and things like that).

The boat does need upkeep, but it's pretty minor. Varnishing, bottom cleaning($50 every couple months) and the big expense is every couple years it's around 1k for a bottom paint job. It's paint that keeps sea growth off the boat. Eventually you do need bigger "house type" expenses, a new set of sails would set me back 3-4k(every 8-14 years maybe), I have a 1994 engine that I may need to replace 10 years from now(7k to do that). But those are easy to manage since you can usually plan well ahead for them.

In Florida my slip + electric costs around 520 a month. Other states can be cheaper than that. My slip fee includes free wifi but I have a 3G setup for internet as well($80 a month). That'd handle my internet while cruising as long as I stay coastal.

Satellite internet is way too expensive, so everyone uses long range wifi(like home wifi, only 5 miles of range) and 3G/4G.

You can find out more information here http://www.livingaboard.com/forum/

And this book is pretty good: http://www.amazon.com/The-Essentials-Living-Aboard-Boat/dp/0939837668/ref=sr_1_1?ie=UTF8&qid=1334777701&sr=8-1

If you're interested in books, I bought this[1] one. It's a pretty good starter. I also bought an older used copy of Chapman Piloting for general boat knowledge.

I personally haven't decided for or against doing it (the possibility is still a few years off), but at least it didn't scare me off entirely. I recently bought a house and the amount of maintenance makes me want to go as far as possible away from maintenance (e.g. getting a super solid tiny house, metal roof, etc) which is not a good point for a boat.

As far learning how to sail, there are "accredited" courses which include time on the water. You can also go outside that and probably get training cheaper. Look up local yacht clubs and see what they have (we have one even in landlocked Austin). I haven't gone farther than research yet so that's as much as I can say.

[1] https://www.amazon.com/Essentials-Living-Aboard-Revised-Updated/dp/0939837668/

This was a great resource for my wife and I (boston, 42' trawler): https://www.amazon.com/Essentials-Living-Aboard-Boat/dp/0939837668.