I agree with Craig, keep it loose and organic. I’ve had several wine groups over the years, but the one that has worked the best and lasted the longest, grew organically from my close circle of cycling buddies. Only two of us were wine “geeks” to start but each brought something interesting to the table, besides great friendship and company. One is an amateur chef, so he coordinates our dinners. One’s wife is an amateur pastry chef, so he brings dessert. One prints money so he tends to bring the MacDaddies. We name a theme but do not mind if it strays a bit, in fact, we laugh so hard about it almost always straying. We don’t get all geeky about tasting blind, trying to drink 4, 5, 6 or so wines side by side, or even taking notes (I do, on the side, with my iPhone note App, trying to avoid detection for fear of being razzed!).
I normally coordinate the order in which we pop the wines, and I normally serve the wines (me being the geekiest in the group), mostly because my biggest issue is serving temperature and decant time. If I wanna get anything right - over all other issues including the type of glass we use - it is serving temperature. We will chit chat about the wines, sometimes the discussions evolve, sometime we segue to talking about football, cycling, ladies, politics or planning our next guy’s trip.
We have no set rules on the number of bottles or even price. Some of us can afford more than others, so if we can, we are generous. Some of us bring 2-3 bottles of higher end wine, some will bring dessert and a decent wine, the chef might not bring anything as he did all the work. With no rules, somehow it always seems to work quite well. Part of that is because two of us in this group will always step it up a notch, and I’m good with that.
At the end of the day, I only want to be in a wine tasting group if I genuinely enjoy spending time with the people. My time is very limited and very valuable to me. A bottle of Haut Brion in a group that does not stimulate me will not lure me to the table. I’d rather be at home with a great $25 Chinon, quitely contemplating how incredibly good wine can be even at this modest price-point.