Some of that is just part of the business, potential tenants don't know what they don't know and some will be tire-kickers.

I don't want to pay them over $1500 to do nothing, but I am also tired of working with them.

When I got tired of the drive I sold it.

My 1962 builds look tired.

I got tired of my landscaper charging me to mow the grass in the offseason and installed turf. 

Drive for dollars.Do you want tired landlords?  

Even the ones that do allow them, may have a fair number of "locals" living there, and if they get tired of the extra trash or parking issues, they can make a stink. 

If you are tired of managing 26 individual insurance policies I would look into a master portfolio policy and put all 26 properties onto 1 easy to manage policy.

This shows me your version of 'financially healthy' is normal, as in the same tired vanilla ways generations past have kept themselves working for someone else for 50 years. 

They are the largest demographic segment we have (about a quarter of the population) and they are new to the real estate market, but their are tired of paying rent (the oldest millennials are now 38) and make 40% of our buyers.