Once I have a few kilts in my wardrobe, I'll start wearing them more regularly, for the comfort factor. for the moment, my kilt is for special occations.

I'd say its easier to go from pants to kilts then vice versa as moving to a kilt is a reduction in stimuli. Habituation is a well known fact, I do martial arts on an off, and it always hurts when I get back after a break. After a while, the aches and pains fade, but we all (at the club) know they really go away, you just get used to the beaten-up feeling.