My husband has a very sophisticated palate...he can detect cherries, tobacco, etc. My palate is bimodal: I like it or I don't.
We made a trip to Minnesota last year and came through Iowa....stopping at several wineries. We stopped at La Vida Loca....a winery at Indianola....my hubby had noticed on their website that that made a Jalapeno-Raisin Wine. This must be a hobby that has gone very bad....none-the-less, the Vitner was nice and, as always, we had a good time visiting with the people that had managed to find their way there too. The Jalapeno-Raisin is sitting in our cellar....someday we'll take it out and try it....we have a set of recipes that we got at the winery for some marinades....that probably will work.
So, the way to make the neighborhood thing work is just do it. One Friday night put a sign at the end of your street announcing the event. Set one table out and some chairs. Make it simple so that it truly is bringing whatever you have on hand. Ask someone who comes if they will host the following month. You don't want cost to be the barrier to getting together.
In Central Texas we can do this year round....up MN way you'll have to adapt for the winter months....oh, that's a good chunck of the year up there....my sister used to live in Owatonna. Take advantage of the spring and summer to get it going...you will figure out how to manage by the time the first snow falls.
Let me know about your next good label...perhaps I can find in down here.