I know many HOA's won't release documentation to a buyer purchasing within the community until after appraisal and inspection of a property are complete- and then, I'm not quite sure how clear their books may be or how strong of a predictor they would provide in your estimations of future special assessments. 

I've used Erich for all my inspections on the south side, he is great. https://brickbybrickinspections.com/

I don't know if the tenant will be able to get a traditional loan as it may not pass the inspection requirements.

One thing to note is make sure you get a good inspection!

Will the seller allow you to do inspections?

The issue was suppose to be taken care of by the final inspection but wasn't.

I know I’d also need to get someone in there to inspect the place to tell me the things that I may not know to look at.

They should have a deferred maintenance program set up to keep your property in great condition, they should be doing yearly property inspections to make sure your tenants are keeping up on the place, and they should be getting you rent increases each year to keep your ROI increasing with the market.

This also includes the initial inspection, final inspection and dust sample analysis.

He can explain about the inspections and answer any questions bring confidence to the agent and seller.