The HOA may have a monthly fee but you can often get hit with a "special assessment" that wipes out any cash flow. 

If you can make repays and the numbers still work then your good.You can walk the property and look at pictures for big issues but you should get a property inspection done and bring in the appropriate contractors to assess and estimate repairs for any issues. 

I agree with your assessment about positive employment trends.

There may be some slick people on BP with a formula for you to calculate rehab cost, but to be safe you should really get a GC or two in there to assess the situation and provide you feedback on potential costs. 

Properties have not been assessed since 1983.

Sure, put in the money it takes to keep the place running day by day (i.e. operating expenses), but avoid major capital upgrades until you have title.In the end, it's going to be the Buyer's responsibility to list the risks, assess the likelihood, and take reasonable preventative measures.  

That way you get their eyes and systems assessing the deal and you learn why it is or isn't worth doing without risking any of your own money.Alternatively partner up with someone who is looking to do a flip and offer to help them for free.  

I'm running into a catch 22 where I can't determine my ARV because I don't know what my CAP rate will be and I can't assess my CAP rate because I don't know what my ARV will be. 

Basically the bank has the property inspected and value assessed. 

I’d also like to mention I’m assessing these as bringing “hustle” into a deal.