Losing money in equities happens to people with an inadequate asset allocation, as they make the mistake to sell during a downturn. 

If you are going to be renting to riskier, lower income tenants already, you might as well do section 8 and have some or all of your rent backed by the government.

Because of my age, 59 1/2, I can take some, or all of it if I wanted, without penalty.

If not, think about converting to a Roth incrementally or all now while taxes are low.

I don't like when people say things like "it's too late" or "all the deals are gone"...as if there is a finite number of them. 

If that is the case, unless they stop paying or violate other terms of the lease I am not sure what grounds you would have for evicting them before November.Having said that if they are paying right now, which it sounds like they are, and it is covering some or all of your existing expenses that is WAAAAY better than having a vacancy and all the cash to maintain it coming out of YOUR pocket.

@Jimmy Thomas Try Dekel Abstract or All ahead title or Sunnyside title  

How do I protect myself while having access to these incredible benefits.I appreciate any feedback on any or all of my questions.

If your boss is willing to cover most or all of the costs of obtaining your license and you expect to remain in Arkansas after graduation, you should strongly consider it. 

Look into if a few  or all of your current condos would cash flow better as weekly rentals, especially if as you say they’re in better locations etc and include amenities.Then going forward keep this same model or start investing multi family.Just another way to go.