Borrower gets their money, bank gets their fees, sometimes insurance companies submit invoices, title companies, brokers. 

This meant we would Invoice out possibly a week after receiving all the required materials.

I would include an invoice for the wasted trip.

You could always present all the information you have to them with a repair invoice attached showing the damages and that you will not be giving the security deposit back on the account of this.You may get lucky and they may just agree to just move on. 

One of my tenant's recently asked for an invoice for their upcoming rent payment.

Fast forward to April of this year and my PM informs me of the invoice.

I will also, on request, send the actual invoice from the handyman. 

As others have mentioned: photos, videos, and invoices/receipts have checked the boxes for us when it comes to managing properties out-of-state (I'm in CA, partner is in CT, and we have properties in FL).

It's one thing to say you're going to charge someone for use of your property, and even to invoice them, but how do you plan to pursue payment in the event that they don't pay voluntarily?

Can I generate my own invoice to get applied to settlement statement or are there specific requirements?