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It's iffy at best. Although I see nothing wrong with discounting a portrait, I like to do it with no strings attached. It may seem to make sense to try to arrange a "fair trade," i.e., "If you get me three paintings, I will paint one for you for free." But this gets into a consignment relationship instead of a benefactor arrangement. I have had my success with benevolent benefactors.
I would say the best way to approach this would be to do the straight, discounted commission, (It doesn't have to be a deep cut, maybe only 25% off -- just so they know you are making an effort for them...). Then when the painting is completed, do a delivery and open house with their friends. The friends see the recognizable likeness in the portrait and they see what you can do for them. You could also arrange it so you are there when there is an auction in a local private school that you donate to, or you could volunteer to spend one day at a local elementary school, with newspaper coverage. "Washington Portrait Artist Honors Clinton, SC Elementary with Artist in Residence Program." I call it sandwiching.
You can't really hold your "patrons" to any kind of bargain. You just need to do your best to make the trip successful from your end. A trip to the East coast is still a lot cheaper than running an ad in Veranda, or paying 40% to an agent. If you are ready to do the cross country gamble, you get your ducks in rows and go for it. As I said, the first few times for me it didn't take. But if you are open for sandwiching opportunities, something always comes up. Family vacation in Florida? Hit the galleries. In Naples, I set up shop in a small craft shop and advertised in the local paper that I was running a private showcase. The craft shop was happy to accommodate me because I drew in customers that would not normally come to her shop, and I paid for the newspaper advertising.
Peggy
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