The advantage of the law firm is they will do it every time they come up for appeal and you will not have to pay attention to the deadlines. 

So I had to file for a dispossessory proceeding, but it was short lived because I received rent from him on the 15th of the July.

I did some digging and they had been operating for a long time and had numerous complaints filed. 

File all receipts in a dedicated Google Drive folder.

I'm wondering if I should give the new owner the entire tenant files or just copies of the leases.

Q- How do THEY report the $60K we are paying them for this OPTION  when they file?

For example, moving out a tenant includes about 30 steps like pulling their file, emailing them the move-out instructions, changing the lease in my software to "Active - Notice Given", stopping recurring charges and payments, prorating last month's rent, scheduling the pre-inspection, etc.

Collecting rents is super easy and the bookkeeping features allow me to track all revenue & expenses for each property in a manner that makes filing my taxes at the end of year very easy. 

That said, make sure you’re comfortable with the comps and the exit strategy, whether that’s selling quickly or holding for a bit if the market doesn’t rebound immediately.To overcome analysis paralysis, try setting a deadline for making a decision.

Ray Kroc (McDonalds) filed for BK 4 times.