Head on a J/27 exists but is very cramped and not terribly comfortable to use if that is a primary requirement. We have one on ours and the ladies do use it but is quite an experience for them
Some good suggestions. Nothing ground breaking yet.
There is a J/29 at a near-ish club. A J/80 and a couple Lindenberg 28s in the bay too. The largest race we host has about 40 boats on the line ranging from a J/122 to a Catalina 25. There are only a few pairs, J/24, J/35, and Ranger 29. Everything else is a one off.
The 2 Ranger 29s compete in the weekend races, albeit without spinnakers (despite prodding). So it would make some sense to get a R29, but they are getting pretty old and worn out by now, and barely tick the entertaining box.
There has been a U20, it has traded hands a bit. I don't think it would satisfy the size-comfort.
The issue is the "racers" want to be able to take the boat out for the weekend with the Misses or kids and not be on something that feels like a dinghy. Full headroom is probably not required, but certainly crouching and seated is. I would love to race Lasers or something, U20 would be good for me, but it won't catch on I'm afraid. Need something more substantial.
The head requirement is due to the number of females that would really prefer not to use a bucket. It's not a deal breaker, but I'm sure it goes along way to convincing new owners.
Santana 30/30, Capri 30, J/27 are definitely good choices, but I don't see many of them available within 500mi. J/30 makes some sense, I'll have to research how many are around.
This could be a complete pipe dream.