Then complete your move-out on time and leave the place clean and without damages.

Obviously I realize that the older the building, the higher the deferred maintenance expenses... the worse the neighbourhood, the higher the rent collection challenge, evictions, damage, etc. etc.

IE they move out and you find $2k worth of damages, and then they fight back that they made the place so much nicer how dare you (when the floor was only $500).

You can require the tenant to go through the PM for all repairs, if you don't already... 4) Do you/your PM's require all tenants to carry renter's insurance in case one of your tenants causes unintentional damage to the unit?

As a history buff, I would also love to invest in (and eventually restore) historical homes in the Houston-Galveston, Texas.

For the trained eye, you’ll notice I removed the existing window and plan on replacing it with a smaller awning window that will be at a higher elevation to minimize future water damage.

I am not at all concerned for my personal safety while traveling in Detroit, but rather the damage that scavengers could do to a property if there was ever a vacancy.

If the risk is high, and the insurance company issues you a DP1 type policy (bare bones insurance policy) they will not reimburse you for any water damage that occurs when pipes burst. 

That being said, after a couple of years of pretty much giving the entire SD back because there was no damage, I felt more comfortable with the move in fee.  

Usually creates a smoother transition and less damage tot he home.