If they don't see your post, you should contact John and Laurie Gray - j&lgray - they did 1600 miles of the loop in their R25, Laurie Ann. Sounds like they had a blast. They've talked about it a bit on this forum.
We haven't done the loop, and our R25 is our first boat, so we don't have any experience with a flybridge. That said, it is not the least bit claustrophobic. Plenty of windows and hatches provide an abundance of air and light, and the cabin doesn't feel at all space constrained.
The R29 is significantly more spacious, and with the head moved forward and below in the master berth, the starboard aft corner is open giving you an expansive 360 degree view. Go for it!
Cheers