We have already paid him for this, and now he is trying to invoice us again for it.

dang it loool, I think bird dogging might be my only option then...unless you know some other way.

Should a major expense, a la a roof arise, the management company could invoice the holding company for costs in excess of income and the holding company could transfer funds, write a check, whatever makes sense.

Good Morning Silvestre Madrid Paypal invoices works in most cases beyond your tenants.

Not only that but we can produce invoices and take credit card payments from our phones or iPad and the payments go directly into Quickbooks. 

In her email, she talked about invoicing me for when she had to talk to the utility company.  

When I received the invoice on the day he mails out my payment the $120 was not included.

For security they need to add the difference at renewal, just send an invoice showing security on deposit and what they owe

If so, there's no real question here, you write them up a checkout invoice, and keep the security deposit. 

Automatic late fees and can add invoices like grass cutting