Thank you, everybody, the common practice over here is that when tenants break the lease they do not expect the deposit back at all, but usually they leave some kind of mess behind, so they owe money anyways. 

Realtors here can only legally accept payment of any kind from their broker. 

It also kind of depends on when you started charging them at move in, be consistent to avoid any issues.

It's kind of crazy, but as long as you account for that in your estimate, you should be fine.

The old stuff looks clean and not dreadful, and is in neutral colors, but isn't that nice (e.g. the cabinets are kind of rickety and the DW/fridge don't really fit all that well into the space made for them, the floors aren't missing pieces, but also are a bit uneven in places).  

I kind of work my way backwards.

I have seen a three units in Cicero trade for that kind of money, and they would cash flow very well.

If YOU were the homeowner getting that kind of news, you would have to wait until Monday to get it fixed! 

It is probably a good idea to look at one of each kind, so you can tell them apart while shopping.If you think that any of the windows have been leaking (often around the bottom), you might be prepared to replace rotten framing after you take the old window out. 

I just want to make sure that it is absolutely necessary to obtain both kinds of insurances.