Check out Ebay for "David Clark" headsets
I like the H10-13.4 for the price and flexible boom (great feature)
http://cgi.ebay.com/ebaymotors/ws/eBayI ... 2419478716
Safer bet might be to browse the boards at the airport and see if anyone's willing to sell. I've had students with bad experiences with other headset brands (except BOSE) so I'd stick with the David Clarks.
I have a H10-60 and it's lasted me 11 years so far, only having to replace the foamy part on the microphone 2 times...coming up on 3.
You should be able to find good condition used DC's for under $100 bucks.
Weekend job ---> pump gas, or wash planes at the airport (PSM or Skyhaven), fill the guys plane....get to talking....blah, blah, blah....wanna come along for a ride sometime? CHA-CHING!!
Taylorcraft, taildragger I'm guessing, great for developing your skills and you have to fly it all the way to back to the blocks. The only problem is that it might be a little cramped. If that's the case I'd recommend the not-so-new C172, lots of room without all those fancy do-hickeys that come with the 2001 C172 model (you wouldn't be allowed to use them anyway)
Books - see what books are required, pick them up used. Try
www.dwc.edu (nashua, nh), schools off for summer but the bookstore might have some used aviation books kicking around that fit the bill. When in doubt, Ebay.
Charts - AFD (airport/facility directory)...$3.00 I think, might have gone up
I think it's good for 3 months (memories stretching on this one)
VFR sectional (New York, I believe). As long as you don't go any further Northeast than Portland, I think you're covered; but always check the chart before you buy. $6.00 there, good for 6(?) months.
medical test - 1st, 2nd, 3rd class should be all the same price, over 35 years old might need an EKG, in that case stay with 3rd to avoid the EKG fee. Shop around!!! The guy I go to gives me a first class for $35, ask around for the closest/best deals. Medial is one of the first things you should do.
written - 70 might be on the high side, shop around here as best you can.
check ride - $250 would be high side, I know I've paid it before, if you can find it for 100 - 150 I'd take it.
The more money you can save the quicker you'll be done.