So the seller is essentially saying the tenant is paying 25 days late each month with their permission.

My guess is that you consider many properties as options before deciding to buy one, and vetting wholesalers is similar (look at many, with hopes of finding one).

There is more room for confusion and mistakes.

@Thomas JaskulskiIf it is a good deal, the buyers will be the easy part.

The problem is the HOA doesn't allow VRBO rentals, only year long leases so I wasn't able to generate cash with this property.

He is currently renovating a defunct motel near the Clinic to add even more. 

It IS having a massive credit limit/card...Just my two cents. 

"Is it a common practice to report it as a loss even though I fixed it out of my own pocket?" 

If you are renovating your rentals you need to let the current insurance company know what is going on, if they send an inspector out there within the time you could get kicked from the policy too, and not easy to get back on one.

This also leads owners to ASSUME simpler is better when it comes to management contracts.