I added a "cowboy pool" to one property...now I've got a pool that needs cleaning and most pool companies don't service above ground pools, go figure. 

You hired cleaners to clean the unit between tenants?

If your budget is so tight that you can't handle a small leak, what will happen when a tenant fails to pay the last month of rent and abandons the property with $6,000 in cleaning and repairs?

If you choose not to show up, he would almost certainly be awarded a judgement.Of course, you could choose not to pay the judgement, but then he can send it to a collections agency and your credit score will be trashed.I don't see a scenario here where you get through this cleanly.  

Seems clean, visually appealing and somewhat updated.

We’ve found that traveling healthcare professionals are typically great tenants—responsible, clean, and reliable.

Tell them to get out in seven days, use the deposit for unpaid rent, cleaning, and repairs.

Also received the Scope of Work: roof repair, exterior paint, replace rear siding, new exterior doors, new gutter, soffit and fascia repair, clean and seal basement, electrical repairs and new breaker 100 amp breaker, refinish hardwood floors, new vinyl kitchen floor, new furnace and duct work - Estimated $9,100 total."

In 2019 my mission beach units had average revenue minus cleaning of ~$80k.  

So does he really not need affiliates and referral partners (or) is he just cleaning house (or) is there where he goes full ponzi scheme?