If it was in my power to do this at the moment, I would jump right in, even if you start off small on the weekends. I don't have my big pit yet, to do this as a commercialy testable venture.
If you have the hook up with your local grocery ceo, put yourself on the correct legal footing, jump through the hoops to make it the right way from day one, then load your cooker on a Friday night, cook all night, and see what you can sell from your pit in a local grocery market, from Saturday mid morning, when the last one sells, go hame count the money, and report back here, so we can all add our 2 cents in how to improve next Saturday.
If you also offer to buy your meat from the store and include that fact on your signs, I'm sure you will get a better than competative rate on your meat.
I know that the first step of this journey is a doosie, but once you are over that hump and are legal to sell, health permits and insurance in hand, you can even stretch it out by starting a load Friday morning, if your pit runs well at an even temp, or you have some way or someone who will check on it, to make sure it holds up ok, you could then sell Friday nights too, out of coolers in the same parking lot / store, and have your Friday nght / Saturday morning preheat already done for you.
Man you have just sent my brain into overdrive with the possibilities to do something similar out here in the West. Need to have a shed on the trailer to do it from, or out here you'd freeze in the back and burn in the front.
I'd also think about getting started with just pork and ribs, once you have them rolling along you could try other things.