I'd like to build a good relationship with him and eventually convince him to move some of that stock market money into my hands.  

That is an eventual future step but near term to write a contract to buy its simplier to buy Frank and Dave's 30 days due diligence package.  

I plan to househack my first property and eventually move out in a year or two and purchase another one.

Bad choices all around; my father was an alcoholic who eventually died in a nursing home from end stage liver disease with his brain totally pickled from this disease.Gail

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.