It's part of the problem and this was a great post.When you are one of the voices of reason here or in person, people who like back pats and can't handle criticism always do the same thing.

I don't have STRs there, but I've thought about it since I like to return "home" a few times a year.

Having a solid team around you like agent, lender etc.

I’m not sure what that looks like but if I sound like someone you’d like to connect with then please reach out to me. 

At the same time no matter how much excess insurance coverage you obtain, there will always be a policy exception for gross negligence and even negligence will likely be covered only under reservations of rights meaning the carrier can opt not to provide coverage. 

I own a rental in Ohio and would like to increase my investment (purchase another one or maybe two). 

Narrow down to some areas you like.

Alternatively, he could hire a handyman, etc. to finish up what he was responsible for and he can pay them directly.Alternatively, since you both own it, you could take on 100% of the management and your brother pays you X% of the rent like a property manager.

Ohio really sounds like a good place to do something like that.

It will be an extremely risky proposition and likely end up in failure.