If you are doing a Rent-to-own do you charge a security deposit?

If you accept him as a tenant, require an additional security deposit.

- Does your QuickBooks software reports match up to your tax returns, depreciation schedules etc.?

.) - they will coordinate with the buyer for appraisals, termite inspections, coordinate with their mortgage lender, earnest deposits, etc. - they will be the primary contact, so after you and the buyer have settled on the price and contact a title company, they do all the rest of the work!

Simply write a check from one to the other and make the deposit.

I don't put up any earnest money deposit  so no risk.

You require your t/b to place a 5k or 3% (whichever is greater) option deposit on the property (aka, your profit in the deal), and add that into the price of the property.  

I would contact him and see if you think he would be a good match to manage your properties. http://www.exitrealty.com/agent_detail.aspx?

If there is, pay the bill and deduct the amount from the security deposit.

Step back a bit and figure out if you want a turnover there right now, if they have paid timely and no complaints during their lease term (last owner should have given you the deposit, applications, any leases they signed for him, rental history of late payments, etc.).