The only problem with section is one inspection per year but if you kept up with the maintenance you're fine. 

Between tenant turnover, maintenance, upkeep and the inability to find a decent property management company, I lose money.

Purchase price was $122,500, financed $118,000 at 3.75% the town assess the property at $162,000, it was appraised at $124,000 due to deferred maintenance which I plan to correct within 4 months of ownership. 

I wonder if there's a way to structure things so that there are monetary incentives for the PM when they keep a tenant in place long term (reducing turnover), and perform enough preventative maintenance to avoid high cost repairs that could have been prevented.

It's amazing the credibility you get from your maintenance crew when you show them a product they didn't know about (vinyl planking floors or CU/AL rated outlets for aluminum wiring) or discuss a job with them as if you've done this hundreds of times.  

I also have 15 years experience in building maintenance.

In real estate, any "preventative" maintenance is encouraged; property, vendors, relationships, or otherwise.  

Are you prepared to deal with tenants, maintenance and the property managers? 

You will want to have the accounting, maintenance and everything else in line so when you have 50 properties your not sitting at your desk looking at a pile of papers.   

Look for someone with a similiar portfolio to what you are trying to accomplish.Finally, ask questions but don't be high maintenance.