I understand wanting your tenants to have insurance, but as a person shopping for a place I would likely look at that and think "this management company will be a PIA" and move on.

There is also the PIA/longevity factor, a trouble free tenant there for a while vs one who calls you all the time, this does not contribute much but does contribute some.

As for the historic district, they're a PIA from an owner's perspective.

Have you tried hiring a PI? A

But since that is a huge PIA, you probably won't want to do all that.There are also products designed to go in between subfloor and hardwood floor, like this:  https://acousticalsolutions.com/product/iso-step-floor-underlayment/And of course if you are considering ripping out the subfloors, you could go with a thick wall-to-wall carpet on top of a thick pad instead of hardwood.

I mean it snows in The mid west so I would think its a PIA to move.

Yes tenants can be a PIA at times, but if the communication is clear and expectations are front loaded, I think some of these heartaches can be avoided.

And, if nothing else, I personally like the opportunity to see if an applicant seems like they are going to be a PIA before I sign up to having them in my life for a year.

@Mark AndersonMaintenance issues are a PIA when it comes to appliances, but whether or not to provide them depends...I've tried not to provide appliances, but all my units are priced well above other rentals in my area.

I agree with Peter, the parents are the biggest PIA, leaving them off the lease solves that problem.I make them all read and sign a document that explains how stuff works and how to solve simple maintenance issues.