Sounds like you could be handing them a check for $200 along with an invoice for $2000 to cover non-pet issues.  

Do they just include all payments in one monthly invoice?

And you haven’t even started with the paperwork yet, filing monthly taxes, sending invoices plus the numerous emails from owners and guests.  

I understand the total roof replacement cost is way more than the single item/invoice limit of $2500, so it may not qualify?

My friend gets his 20k back plus interest and I would invoice him for the difference.

I have a C-Corp through which I invoice my brokerage for commission checks to keep tax payments at a minimal (at some point it made sense to incorporate).

They have an investor that they collect the rents for, take care of all his accounts payable, work invoices & run the entire 13 properties on quick books.They also issue the 3 day pay or quit but the attorney does the evictions per se.

Now HML broker has sent me an invoice for $3,500 demanding I pay it immediately because he fulfilled his contract obligation to me.

I use QuickBooks for my bookkeeping, so I just set up automatic invoices that go out to all of my tenants on the 24th of each month.

I gave him a 50% down payment after a signed contact and invoice on the down payment.