You could look for a closeout/last year's model helmet like at Nashbar. I have a Giro that I like a lot, but I think anything in the $80-$100 range is going to be very comfortable. As long as you don't crash, you can keep it until you get tired of it, and if you _do_ crash, the better it fits, the better protected you are.
Sierra Trading Post has Sidis, MTB shoes for like $60 and Road for $100, regularly $140. Closeouts. The womens MTB shoes are small sizes, but maybe the mens? I would recommend getting the best, most comfortable shoes you can afford. I've had my Shimanos, about $80? for five years I think, and they are like new. I've bought a ton of shoes mail order- I just order a couple different sizes and send back the ones that don't work out.
Sidi, on their website, gives this advice for fitting shoes: Go at the end of the day. Try on your size, wear them for 20 minutes to give them a chance to warm up to your feet. Then try on the next size up and down, also for 20 minutes.
Nanci