The downside will have more to do with your business personality.

And they’ve cost me alone well over $30k in damages and lost rent thanks to their complete negligence.

That’s how the wealthy do it with real estate or businesses.

I was chatting with some of my lending buddies at big banks and they are all backing away from the CRE space including office because operating costs are increasing more quickly than rents.

.🔹 Insurance Challenges – Even when insurance pays, it rarely covers the actual cost to completely rebuild.

Anything you do remote will come at a cost of operational inefficiencies and a higher cost of doing business.

Quote from @JD Martin: If you have found people willing to lend you - someone with I assume no experience doing this, since you're here asking the question - 100% of the costs of such an endeavor for half the profits, you have found a gold mine and should look no further.

Nights, weekends, holidays, etc.To keep this on-topic, though...DO figure out what's healthy for you to manage but remember it's a process where every experience teaches you good and bad (and be patient with that process).DON'T sweat the small stuff (damage/costs under $50, undisclosed dogs, etc.) but DO find a way to learn, prevent, put in better practices to maintain your sanity. 

I have questions about their business acumen though.

The purpose of any business is to grow.