The fact the associations force agents to join is a questionable tactic. 

We too were forced to convert the land contract into a note and mortgage, at a huge reduction in the loan balance I might add as well. 

So, the question becomes when things get hairy is can you FORCE them to pay.

Purchase price: $288,486 This was our single-family home while stationed in Oklahoma with the Air Force.

I would either use a HML spread over multiple deals to rehab or I would find a property with good bones (foundation, and most studs/joists are solid) then buy it for super cheap and force appreciation through the rehab, which is what I do. 

Buy a forced-placed policy if you must.

Keep in mind, though, it will require significantly more time and effort but offers the potential for higher rewards through forced appreciation.If you aren't wanting to be as hands on with your real estate and want to approach it more as a side hustle while you focus on your career, the turn key option may be better.

I am curious about any potential barriers to look out for- timing, access/cost supplies, labor force?

When I called yesterday they said I had only 3 days to review so, I'm now forced to use the system. 

This does not mean you can leave the unit vacant for 6 months (not that I'm accusing you of wanting that) but it also does not mean you can be forced to accept a less desirable tenant nor can you be forced to lower your rent.