We have two houses and don't know what to do with them...

[Jason Hillenbrand]

Hello BP!  First post, here we go... I think I have the world figured out (ha) but would like this community's take on my situation if I could bother anyone for advice.  

My girlfriend is studying to become and agent and I have been actively searching for deals and lining up financing for when I find a decent opportunity.  I am a contractor and would like to start building wealth by owning my own RE in addition to my day job of fixing everyone else's properties up.  We both own our primaries residences.  I have a single family, she has a town home.  Her place is worth about half of mine.  I have a little more equity then her but her place is much more "tenant proof" and desirable as a rental and would actually cash flow 150-200 dollars even with Cook County Chicagoland taxes.   My place is getting older and probably has some capital expenses coming up so not sure the risk to rent it would be worth it, but it is in a very desirable neighborhood (school).  We are looking to move in together relatively soon, so as far as I'm concerned, we have a few options...

1) Sell both places, use equity for down payment on a duplex/triplex to house hack.  Tough to find deals that work around here.  Not impossible, but tough.  

2) Rent her place, she moves into mine, she buys a flip, brrrr, or buy and hold rental 

3) Sell both places, buy a live in flip for 2 years, rent, then repeat, (sell before 5 yrs or 1031)

4) Rent both places and live in an RV.  (kidding, sort of)

5) Don't get our personal living situation mixed with our business real estate situation and just try to start investing with private money.

Or any other strategies I'm not thinking of that would get us going and on the fast track to level one financial freedom?  Thanks, would love to hear what you guys think.

Jason