Check out the gear - assess the seams, set up the tent and test the waterproofness with a hose in the backyard, weigh it, and prioritize - what you want to replace vs. what you must replace. Decide where you want to go and check out regulations in that area - there are websites for every major park, wilderness area and national forest to provide info on permits - and what kind of bear proofing is REQUIRED versus what kind you have and are willing to use. Figure out what size tent you are willing to tolerate and check out tarptent.com, hammockforums.net, six moons designs, gossamer gear, campmor, and sierra trading post.

I just got a windshirt and fleece jacket, both Marmot, at Sierra Trading Post, as well as a $99 pair of Keens, for better than half off by combining a coupon with a sale - paid a hundred bucks for the three items. I was in REI the other day and saw similar gear that added up to better than $300. The more you read and learn, the easier it is to make choices on deeply discounted stuff.

Some stuff you don't necessarily cut corners on; I initially picked up a very inexpensive tent, but later found that a hammock suited me better, so picked up a used Hennessy on ebay. Then as I traveled up the hammock learning curve, I understood my needs better and upgraded to a Warbonnet Blackbird, which is hardly ever found secondhand and never on sale, but worth every penny to me due to the features and the size of the hammock. Had I not taken every step on that path and willing to spend the time and money, I would still be thrashing around on the ground not sleeping a wink and would have given up backpacking by now. I had a similar path with backpacks. If you were wearing a pack you didn't have sized before, like I was, go get measured for pack size. You could have grown in various dimensions, you might have had the wrong pack and tolerated it, or whatever - but the pack is an important piece of gear to have fitting as well as you can manage.

Welcome aboard!