I keep a very healthy amount of reserves to avoid using my insurance unless I have a catastrophic issue.

You can point out spots like nail holes where they hung pictures, dirty spots in the apartment needing cleaning, blown outlets they are overusing, etc.

I'd also look into property taxes and what is included with that $800 condo fee (that is really high though guessing it may include weekly cleaning). 

He does not want to deal with the headache of tenants cleaning or any thing to do with STR.

.: I haven't passed this past legal review so for what its worth: Part of my standard requirements for everyone include income is at least 3X rent, minimum credit score, say 640, Clean record and no evictions as well as deposit is paid in full at signing of lease and 1st month rent is paid in full prior to handing over the keys.

Luckily this apartment just needed touch up a cleaning.

A clean, neutral-looking curb gives prospective homebuyers a chance to visualize their own additions/upgrades.

By all means give them a note on how to use all of the appliances (eg clean out the lint trap on the drier after each load, do not use dish soap in a dishwasher, change the furnace filter regularly, etc).

Initially, our plan was to fix the drywall leaks, clean out the property, and relist it for a small profit.

Initially, our plan was to fix the drywall leaks, clean out the property, and relist it for a small profit.