If I may chime in, we grow primarily for restaurants. It sounds as if your initial customer understands the tomatoes are seasonal and is more interested in quality than anything. Make sure this is the case and if so deliver quality product and service. They will pay your price. then they will tell other chefs. They may be highly competitive but they talk. (we just had an industry wine tasting here yesterday. I had the chef owner of the #7 Japanese restaurant hanging out in my kitchen with the 2 chefs prepping food from our farm and another so they do talk). We sell by the pound and we tell the chefs upfront. Definitely look at the unusual, rare types but pay attention to flavor. Definitely grow other veggies, don't put all your eggs in the mater basket. you might want to research chefs garden and learn there story.
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