I live in Denver and she lives in Jacksonville. 

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.)

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

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.  

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

I can totally live with these numbers.

Hello, I am Randy Ivey, I live east of Conroe, Tx. .

My son lives in Davis County and has his own personal window company and 12 houses worth $500,000  in great neighborhoods. 

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.