Reddit mentions of Baratza G 285 Maestro Conical Burr Grinder

Baratza pretty much has the middle of the household grinder market locked up. If all you're grinding for is drip, a Baratza Maestro will set you up nicely. I have a Virtuoso and use a Maestro (the old Solis one before Baratza bought it) fairly regularly at a friend's parent's cabin. The Maestro runs faster due to a lack of a reduction gearing, but runs very quietly, even in comparison to my Virtuoso. It lacks fineness and adjustability for espresso use, but for drip or press it'll work just great.

Mmk.

Let's ignore the espresso machine route, and go for something that will give you strong coffee. Either a moka pot, or maybe an aeropress. (I personally recommend the aeropress.)

As for the milk, the cheaper route would be to heat it up (microwave?) and then use a milk frother to blend air into it. You'll get these big bubbles as opposed to microfoam like you'd get at an actual coffee shop. OR. You can go for a stovetop steam wand like this. You'll need to invest some time/money into this to learn how to make microfoam, but the results will be worth it. I'm actually about to embark on this step :/ (Note, you don't HAVE to foam/froth your milk. It just makes it a little tastier.)

NOW. Back onto the coffee. So we have your "machine/maker" figured out. Let's talk about the ACTUAL coffee. Depending on what you've picked from above, you're in $30-$100+ deep. If you have a local roaster, that's great! Buy beans freshly roasted from them. Learn from them. Ask them to make recommendations. If not, there are a few online sources good for buying roasted coffee. Remember, buy what you can use in about 1-2 weeks. Longer than that and you'll have stale coffee.

If you can, you should buy whole coffee beans, and grind them yourself. The cheaper method is to buy a hand grinder. The Hario Skeleton/Skerton is always highly recommended. A few drawbacks to this, but you'll learn about them on your coffee journey. (Don't want to bombard you with too much information for now.) The Hario Mini Mill is also a great option, especially for travelling, but grinds less.

As for electric grinders, the Baratza Maestro is a good entry level burr grinder, but at a pretty steep price :/ Note: always buy a burr grinder, and note a blade grinder. Bear in mind that using the hand grinders is actually quite a lot of work, especially if you're not a morning type of person. The entire Baratza line of grinders are all highly recommended, but as always, the better the grinder, the higher the cost.

Since it doesn't sound like you're poised to dive into the insanity that is espresso, here's what I'd recommend for a top notch drip setup:

• Clever coffee dripper $13.50
  
• Baratza Maestro grinder $99.00
  
• A good scale $30-$50
  
• A good, quick thermometer $15-25
  
• A kettle where you can easily control the flow rate $40-70
  
• Beans from a quality, specialty roaster
  
  On that list... the grinder is really not optional. You should get one that good or better; it makes or breaks the setup. For the brewer, you could go with any other pour cone or a french press instead of the dripper and get great results. The scale probably isn't optional. The thermometer probably is. The kettle is definitely optional but makes things easier to manage if you're going with pour-drip. (It doesn't matter for press.) The one I linked is the best of its kind.
  
  With that setup and coffee from one of the roasters on that list, I'd say you'll have a hard time finding better coffee anywhere outside your home. As far as how it appeals to someone who likes "caramel macchiato" drinks from *$, I'd add some quality syrups and some good milk to match her taste.
  
  Off the list of roasters I linked, I order most frequently from Klatch, Gimme and Counter Culture, and have loved every single roaster I've tried from that list.

If he's patient and really passionate about his coffee I recommend a vacuum brewer also known as a siphon pot. A safer option would be a nice burr grinder since using preground coffee is akin to buying peeled garlic.

For actual coffees I would echo the Intelligentsia recommendation and add PTs, Terroir - close to you, or Stumptown. I would exercise caution on buying really nice beans, though, since light roasted high acid/fruit African coffees are a far cry from the charred milky beverages most people are used to.