Lot of questions James, but I'll try to answer several...
If the long-sleeve shirt is a Tee, I always put it on before the short-sleeve. Otherwise, the short sleeves are a pain to untwist.
As for the pants, I'd be in between, too. Buy the longer ones, and either just wear them, or have an alterations service cut and hem the legs.
By the way, who offers the Cap 2, Cap 3 and Icebreaker things?
