I was originally trying to focus on fix and flips but as I learned more about financing realized that I could probably go straight to buy and holds which was my eventual goal.

We didn't know anything about the market and had to start from scratch, but it was a great learning experience and gave us confidence to eventually replicate the process in other areas. 

Eventually, they will have to come to terms with the fact that they are not going to be internet billionaires and they need to move out of mommy's house and into their own place.

I believe our paths have crossed before in the triathlon world (a world I haven't been in for over a year, but plan to get back into, eventually). 

Eventually builders will build more sqft in the city, and that oversupply will send prices crashing back down to an equilibrium level (or overshoot to become cheaper than equilibrium)I haven't looked at Miami in a long time, and I don't have a sense for what the situation is right now, but I'd listen to whatever the numbers were telling me rather than force it.

Thank you probate weasel.While you might get through this file eventually, it will unlikely to be worth the hassle unless you have masochistic tendencies.

This also yields tenants more interested in eventually owning a home ("well, we will need to buy a fridge in 3 years anyways, once our down payment is saved... may as well get it out of the way"), meaning they have plans to move out in 2-3 years, thus auto-solving my problems with rent control.

Eventually I'd like to have multi family buildings but I'm not sure what the best path is.I'm interested in flipping/rehabbing but I'd have to travel 2-3 hours as my home market is too expensive for me.

So, in a nut-shell, I am very interested in using wholesaling to enter the real estate investing market, eventually tapering off into rental properties for the passive income, and I would love your input on this!

Set a plan, follow it and eventually you'll get to where you want to be.