The roof might be an expense depending on the specifics of your situation.I would also get a contract and invoice for the $8000 quote that notes $1000 payments being applied from rent monthly.

.: Thanks  for the insight, they ended up adding an invoice to the escrow statement. 

I take the invoice and I pay them the amount of the original quote.

I provide scanned copies of all invoices, but that's my business model.

Property manager had pest control come and they mentioned “partial exclusion” on an invoice, and calling the pest company I found records that they sealed up those drains.

Apps like PayPal, Certified Cashiers Check or Money Order, or even invoicing through apps like quickbooks for them to pay are also great ways to collect. 

Send lease with esignatures.io and first payment invoice through Hostfully5.

Charged me $1700 for the pro group in sleezy way (never issued or emailed one single invoice or pre-notify that the next monthly charge of $99 would occur).

At this point in time unless he comes way down off of his invoice I don’t see any way around this getting ugly. 

@Mary Jay, to layer on to Connor's comment, while some lenders will only pay draws on invoices paid with lien releases, there are also some that will allow you to submit draws on invoiced work.