I have 2 townhouses with property management in place outside of Fort Rucker Army Base in Enterprise Alabama. 

We drank the kool-aide.

Worst case scenario, you can get eyes on it and formulate a game plan, possibly a band-aid until the HOA gets their act together. 

My wife Jen is an instructional aid at my children's school.

You'd need to enlist the aid of a Qualified Intermediary to execute a 1031, and there are some specific rules you need to adhere to, but since you'e not on the market just yet, you have plenty of time.

Having all the separate LLCs would aid you in protecting your investment if you manage them all correctly, but your profit and time will be hit hard.

Just has to be insurable.FHA won’t cover a loan for any commercial enterprise (5 family plus, or other commercial operations). 

Hunters Point  the one over by the cow palace, the one were OJ simpson grew up.. probably about 20 of them most in prime locations.. and all turned into mini ghettos.they now for the most part have all been torn down and repositioned.maybe if Portland wants to create housing for low income they simply need to do the same. the CITY needs to build it and provide it and run it.. why force it on private enterprise.. private enterprise just leaves the market..

I'm really close to getting my license to aid with investing (getting MLS access to view comps, looking at houses on my own schedule, etc.) and need to find a broker to hang my license under.

I've heard good things about First Enterprise, too.