I have been consuming as much education/reading regarding out of state investing as I can as well as literature regarding buying larger buildings (not quite the syndication level) although I have been reading that material as well to digest.

You may be able to lean on the title company if they missed something, but generally if the deal closed and its not an issue of material disclosure or title or something its generally your issue now, the owner doesn't really have an obligation to comply if they closed according to the CD you signed.  

Wow, that’s a tough lesson, but one so many of us in real estate can relate to.

That is true with almost any material item.

3) Special Assessments - Back in 2010 and 2012 there were some material special assessments totaling ~$10,000.

Maybe go to one in a tough neighborhood so you really get in the thick of things. 

As for the decision, it's really tough for any of us to say without knowing your goals, your situation and the numbers on this particular house.

The market is TOUGH right now for LTRs and STRs.Hope this helps - we are trying to protect you.

(Currently our rebar supplier is behind 2+ weeks and these materials were ordered 45 days in advance). 

The IRS may scrutinize such transactions, especially if the "swap and drop" occurs too close in time.If the partnership has to be dissolved immediately it will be tough to sell the one property and defer taxes individually.