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Just to throw out another option...
We worked a deal with Kobe Leathers and they are throwing in a pair of gloves (and sometimes a back protector) with the purchase of the leathers.
All for under $500! On top of that, they donate a set that we give away to a lucky TTD rider.
More details are here...
http://www.tonystrackdays.com/catego...e-leathers.htm
As for helmets, at TTD we're just looking for a decent helmet in excellent condition. We're not real picky on age, but like to see under 7 years or so. As for boots, just be sure they are motorcycle specific and cover the calf area.