I was thinking about this more last night. Thinking if it were me and my company not just someone I don't know.
First off we have several prepay customers each January I get a big check for the whole year. Did I offer them a discount? No they still prepay cause it is easier for them. If they asked me for a discount would I? Yes probably up to 10% Maybe 15% but I would do this only knowing they fit into our route, and knowing they are great customers.
Now if I had a prospective customer as for a prepay discount would I? Yes. It takes too many man hours to gain one account and the average cost per new account for us range from 40-70 dollars pending the year and approach.
Thinking after the first year and the guy not being a PIA you will come out a head and possibly pick up more of his rentals or new customers from this guy.
I know people that buy rentals and they usually just don't buy one, when they can they will buy another and so on and are usually in touch with people similar to them that own businesses and or rentals.
This could be a good in, but keep in mind you still need to make a profit to stay in business and don't put all your eggs in one basket.
What ever I do I must do it right!