I believe it is over priced (originally for sale by owner for $280k,later listed through agent at $360k), but I feel like the seller may be open to a creative financing option. 

Current owner says there weren't impacted the last time it shutdown.

Why did the former owner not execute this strategy? 

I have experience managing this on multifamily properties as both an owner and a lender.

In your case, transferring the property from a revocable trust to an LLC where you and your wife are the owners should not affect the 1031 exchange, provided the LLC is a disregarded entity for tax purposes . 

In the last 18 months various states have instituted new rules, regulations or laws related to (1) need for licensure to wholesale (2) restrictions on marketing of a property in which you do not have ownership and (3) disclosure requirements when dealing with a homeowner that makes it clear to the homeowner that the contact signed with the wholesaler is not a definitive “sales” contract, therefore making it less likely home owners will sign4.

The units are all sold so the owners make up the HOA, but without a board the only person calling meetings right now is the Management company. 

The answer is yes, but it is generally found when the owner is also living in at least one unit (aka "House Hacking").

You can find qualified buyers that are small business owners, tradesmen, etc just have someone qualified to do prop underwriting be fore you sign the agreement. 

Nor any commercial lender, because the previous owners ran it as kind of a retirement hobby and the historical P&L's were crap.