HH60 -- I have seen both, but I would venture to guess that more squadrons have the tac and non-tac guys. Even if a squadron gets everyone their quals, there will be those that will never fly any of the big events or missions -- just plane guard. Their qual won't be worth the paper that it is written on.
As for structure -- HSC CVW will have 8 a/c, HSC EXP will have around 8-10.
As for getting pilots their quals -- I think that everyone can get their quals. The squadron just has to focus on maximizing every training opportunity. I don't agree with how HSC EXP has been simulating (not using actual troops, CRRCs), but still believe that there are enough training opportunities to get everyone their quals properly. Skeds guys need to make sure that not a single opportunity passes.