However since they are a smaller company they don't offer health coverage.

The more diversified you are, the better for your financial health.

She is stating that seeing any roaches or flies is impacting her safety and health as an ordinary tenant.

Looks like pretty reasonable requests from a tenant and necessary for the overall "health" of your unit.

“is there a population of investors that fundamentally prefer buying SFH in deteriorating economic markets for short term cash flow?”

Since you have the benefit of having lived there for so long, you should also just consider the financial health of the HOA and weigh risk of any large assessments.

I contacted my PM and requested if any other maintenance issues come up that are not at the risk of my tenant's safety and health, can we hold off on a few months until I start generating some income.

There are a lot of moving parts and economic tranches of financing usually on the Federal, State, County levels along with private partnerships to make it viable. 

@John Casmon  Totally agree  verbal commitments are not raised moneyyou need to be like the airlines and over subscribe.. you will have fall out.investor wont like the deal.. deal took to long to materialize and money got invested somewhere else.bad news in the economic world investor spooked going to sit on cash. 

Both the new mayor and the new City Council are ignorant of both finance and economics, and will probably introduce rent control in the near future by seeking to have the state-wide ban repealed and then imposing a local ordinance.