Plus there's the question of weather it'd be good for Ukyo to wind up 
with the person she's centered her life around for 10 years.

This is Ranma 1/2.  It takes a lot to be mentally unhealthy here; people do
all sorts of things and have all sorts of traits that would get them locked in
a mental institution in the real world.  Not just Ukyou--just consider
Ryouga's sense of direction, for instance.  Or Akane, who if she married Ranma
in the real world would be a spouse beater.

By Ranma 1/2 standards, Ukyou hiding as a male for ten years because of Ranma
is _not_ an unhealthy obsession.