Left holes in the ceiling for recessed cans but no way of getting a circuit to them without tearing out perfectly good now repaired painted/drywall???

In my approach if a house is on the edge of rehab vs. tear down and rebuild, I would lean toward tearing it down.

A good PM will make sure that the tenants sign a walk through sheet when the tenant moves in, and if they have caused damage (other than wear and tear) they are going to fix it. 

However after doing the walk thru the damages (not wear and tear) will be more then the security deposit.

Invoice:New door handle assembly - $40Door repairs $126Trip fee $150Plus tax So, the door handle was normal wear and tear (not closing properly)I charged them 1/2 of $126 and $150. 

This does not seem like basic wear and tear or returning it to its original condition.

The problem is you will likely have more vacancy, turnover , wear and tear and possible vandalism to your property and units which can add up a lot .I am also curious about how you calculated 25% cap.

That way, you can help ensure you are on the same page regarding what things constitute normal wear and tear, and what things will necessitate  a security deposit deduction. 

You would need to tear off the roof and install rigid insulation on top of the roof and install a new roof.

Also, keep in mind that even the best tenants are going to cause some wear and tear, and if you already paid a lot more for the property, having to fix those things when they move out, is going to add to your overall costs.