@Ben ElliottI live, work and invest in Terre Haute.

For example, living in one, mid term renting one, and short term renting the other?

I live in Denver and she lives in Jacksonville. 

I think one of the easiest ways to start is a house-hack and I still do it myself....Anyhow, I am an investor, realtor and lender and live in Fort Lauderdale so I can definitely give you some pointers in the south Florida market. 

If it's in decent shape, I would do a couple upgrades to appeal to potential homeowners (adding window shutters or bark mulch outside, an accent wall, nicer light fixture in living room, etc. etc.)

@Christian Rodriguez Happy to connect with others from Long Island, I currently live in Brooklyn and work in Jericho, NY. 

If the boyfriend is living there and he isn't on the lease it's a lease violation and you can evict.

We planned to live here for two years, do a "live and flip", and then sell it and use the capital for other investments.  

I'm looking at the proper treatment of the de minimis safe harbor election 1.263(a)-(f), specifically paragraph 6 which details the anti-abuse rule.

I develop for a living and it is easy to buy a piece of land and pay too much because of the cost to develop it.