He's paid:1 - What ever cash he originally put in plus...2 - What ever losses he's incurred over the time of ownership (this would be "zero" if he's cash flowed the entire time, plus...3 - What ever he still owes...in this case $38,500.Since everything else is profit (cash flows), all he really has to do is sell it for more than the total of listed items 1 - 3 above, and he makes a profit....cash flows plus difference of what sells it for and what he paid (items 1 - 3) for it.This is one of the unappreciated advantages of owning rentals instead of flipping.  

Another item to consider: if your contractor can't afford gas to come do a bid, he may lack liquidity and cash to perform his services without coming to you with his hand out. 

The smallest items can help you document your files that this was a surprise and that you really did have the intent to hold for investment purposes.

How do you account for the purchase of staging items?

If you don't have those items in your lease, serve a Cure or Quit.

To be honest I am absolutely pleased with Appfolio,  I just called on Monday for customer support, with a new item, and I had a return pone call the same day.  

I am hesitant to trust a third party airbnb manager over the long term, and even if you have a great management company, there are still a lot of items that are reliant on the ownership.  

You could end up with a non paying tenant or eviction and some major capex item simultaneously.

In NH at least, because of the sheer number of old multifamily building, even on the larger side, a lot of items are grandfathered in.  

There was no process in place for the removal of large items and none of the tenants thought to bring it to our attention!