I worked a beach stand two summers ago in ocmd. Its all about location so make sure you have a high volume/ touristy beach. It's also a good idea to buy two adjacent stands so you can really monopolize the beach and up your prices.
It's been our family business for 36 years in OC. What town are you talking about? OC had the bids in December so your too late for 08. I'm not sure about DE beaches though. I might suggest that you get a job working for one of the operators and avoid the hassels of buying equipment, paying taxes, building boxes, paying the city, insurance, and all the rest. You will probably make the same or more then owning a stand or two.