I went through this process in deciding to grow sports turf and Christmas trees.
First -- ensure there is a market. Lots of people grow Christmas trees locally but the dealers all buy from big producers in Michigan and North Carolina.
Second -- equipment costs can eat you up. Consider what it takes to grow, harvest, store, and transport something as simple as hay [which may not be a bad choice].
Third -- most small scale crops are such because they require intensive labor inputs. So if you are willing to put in the time, heritage tomatoes, legacy garlic, uncommon greens, and the like may be of interest to your local markets and restaurants.
Some Amish families I know send a truck to DC twice a week with fresh greens and some vegetables [plus the occasional snapping turtle]. I've heard they bring back $40k per load distributed pretty widely. The trick is to find the market. They laugh at the stuff city folk will buy like the tops of beets and the aforementioned turtles -- just a matter of taste.