But he eventually spun his inherited wealth into an image of being a smart businessman (despite several bankruptcies, many failed businesses, burning a lot of people and being part of many, many bad deals and scams).

This was not the case of vandals burning abandoned buildings, nor the case of landlords burning building to collect insurance.  

Think of PM like insurance- you wouldn't own a property without insuring it. 99% of the time, things are fine and you don't need the insurance and it feels like you are throwing money away, but when your house floods or burns down, you'll be happy you paid those premiums. 

You're going to get burned if you don't dig deeper and do more research.Friendly advice:)

My best advice is to pick the issues that are of major concern like roof, foundation, radon etc. but perhaps skip the leaky faucet or burned out light bulbs.

I got burned several years ago.

Considering airbnb's downtown, long term rentals in up and coming areas near burns park, fixer uppers...pretty much anything except student housing - that feels hard!  

I have a client exploring a new build (her home recently burned down). 

If you are over leveraged, aren't prepared/don't have a plan to get out, you will get burned easily.

Things like septic pumps burning out, steam room dying, guests catching the grill on fire and leaving burn marks on the hardi siding, emergency bug treatment, above ground pool which is ridiculously hard to manage in our heat & having no time to deal with it if it starts to go, laundry & drying time for all the towels and linens, etc, etc.There are plenty of things we can and will get better at, but I'm prioritizing the stress level of my people as well as the very near disasters we've narrowly avoided, over the little bit of extra revenue we'd generate.