1 Ahh, I see. When you said "Either the raging bear fighting style, or a barbarian who just likes using his fists and knees instead of weapons." you were just being descriptive of the style you were going for with a gestalt barbarian monk, not trying to decide between a normal barbarian or the bear variant barbarian to gestalt with monk. A bear form martial artist concept or a brawling barbarian both sound fine.
2 I might allow a 16 point buy version (each step down I go 8 point buy less) A specific LA +2 race you want to go gestalt with? Or +3 at 8 point buy, possibly even +4 at 0 point buy. A half dragon gestalt with all stats starting at 8 base might be OK, I'd need to think over a specific proposal first.
3 You can come from the Conan world, but Cimmerians will just be humans mechanically.