Sell it and reinvest it in a house hack where we currently live (we are currently renting from a relative below the market rental rates but home prices are very expensive where we live.

I don't know the specifics of where the line in the sand is for you regarding the benefit but I live in a high cost of living area.

Or SFH, live in for a year and then rent.

@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.)

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

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