The second time was because of a broken microwave handle and a broken door in the bathroom (from a party)The third time was stains on the carpet from a petEach process pretty much went the same in that we took photos, documented, and did the repair work then reached out to the guest quickly via Airbnb letting them know the exact cost of the damage and sending the invoices.

Some first time landlords may also ask the management company to handle bookkeeping activities such as paying maintenance invoices or utility bills.Performance metricsThis is the most critical step!

We set up quickbooks to create invoices for tenants.

It also shows when your tenant views the invoice. 

In addition, when a tenant moves and provide an itemized invoice detailing the reason for the deduction.

I keep track of all my invoices, receipts, and upcoming payments with their services and can't imagine doing it any other way--it's so convenient as the apps are right at your fingertips.

You could send a PayPal invoice and just mark "from a friend" so you don't incur the fee. 

Ask to pay by cash and will not provide invoice for the price he asked?

I would get more details or the invoice with specific information on what was performed.  

Invoices from contractors, before/after pics, etc.