Grinds, I find the best time of year to purchase equipment such as clothing is in the off season. Winter gear in spring or summer when the stores are changing over to warmer weather items and then the same is true with shorts and t-shirts. Best time to purchase them in when the cold weather returns. As for tents, packs, etc. decide what you want to purchase and then wait for sales, closeouts, After the traditional summer season is over many stores run sales, also check before and after Christmas. I routinely keep my eye our for items from REI, EMS and Campmor. Most of these stores have websites that will notify you of sales items. I like to try to keep my cost down as much as possible, so I have purchase items from WalMart, Dicks Sporting Goods and K-Mart as well. Good luck,
Barry