So before a work order begins there will be an invoice that is signed.

So you don't have to mail out a bill (an Invoice physically) just shoot over an e-mail.  

That changes everything, Willey doesn't need to lie or deceive any more, he doesn't put himself in a position that he needs to pull tricks or play games, dang, he can be truthful! 

If it was a lot of damage, I would invoice each job separately (drywall repair, door repair, door casing repair, etc.).

Keep receipts for parts/materials, invoices for hired services, and yes charge for your labor if your jurisdiction allows it.

I would be fine with dropping it off at a office, however for me I have tenants in two different towns and it's a 30m drive between them (meaning 1hr round trip) which can kind of make it difficult for a tenant to do.I'm still leaning towards sending monthly invoices showing them what the rent is, due date, ect so that what they pay/when they pay is put in front of them every single month.

I sent the settlement letter and invoice to general delivery (no fwd addresss, of course) and a copy to the section 8 office.  

(Even though I'm just really dang good from experience). 

There is nothing quick (or inexpensive) in manually keying hundreds of monthly transactions from an owner's statement into Xero or QB, even with recurring invoices set up.  

With IPN, I could have it bill the tenant automatically, now I have to generate the invoices (I have them set in QB to generate monthly, but I still have to log on to actually send the invoices).