Maybe the professional inspector has  historical knowledge about the property or knows of other tradesmen that do. 

I recommend all new RE investor invest local in part because of this issues you list.You live in a market that historically has produced one of the best ROI in the nation but you are considering investing in the Midwest where there is minimal appreciation, is remote (need to build and manage a trusted team), has cash flow that typically reduce with time compared to inflation.Compare to San Diego market that has a long history of both property and rent appreciation, that is local for you to have more control/oversight, has historically increasing cash flow.We invested out of state (still have a single OOS SFR) and it did not produce the ROI like our local RE investments. 

Our philosophy, vetted investment opportunities, means we focus our efforts in locations and segments that have historically provided stability, and are currently undergoing above average economic and demographic growth.

I don't love the area, but it has about a 95% historical occupancy.

A lot of investors typically avoid these because of the initial costs and length of time it takes to do the work, but I enjoy the challenge and would much rather do a major renovation on a historic home than multiple cosmetic remodels for the same amount of initial capital and return on investment.

I understand we've kept them at a lower rate to ensure their stay because historically they've been great.

HOAs are not always receptive to providing financial data or historic data regarding assessments (could be an indicator of poor maintenance budgeting) so you may want to use your realtor as a source to pursue getting details about the leak and the financials.

I use far lower than San Diego historical property and rent appreciation numbers. 

Area code 77701( Oaks Historic District )  specifically. 

I guess on a basic level but historically interest rates have little effect on housing demand and I don’t see if dipping much as rates rises.