Facially simple question: If you had to start backpacking (and purchasing or making gear) all over again, where would you start?
First, a story: I discovered REI during my first year of college and I spent hours perusing its racks. My first purchase was a 4400 cubic inch backpack that weighed 4.25 lbs (a full 4 lbs more than my lightest backpack right now). I also bought an REI Halfdome 2, which also weighed somewhere north of 5 lbs (including footprint and stakes).
My lightweight epiphany came sometime after these purchases when a friend of mine showed me his homemade silynylon backpack that was designed on the frameless packs of Ray Jardine. I was floored. Here was a backpack that weighed in at 16 oz that had the same functional capacity as my heavy, overbuilt backpack.
So where would I start? I would read Beyond Backpacking first, and do it at a time before 1999 when I went to Isle Royale with my scout troop. And I would have thrust myself into the make-your-own realm. My mother is a fantastic seamstress, and I would have asked her for her assistance. Back then, my funds were limited and the thrifty nature of making your own appealed to that nature. Making my gear early may also serve to limit the consumerism pressure to constantly exchange and replace gear for lighter alternatives. This would have put me in a good position to develop my so-called "Big Three" (shelter system, sleeping system, backpack system) to somewhere near four pounds (1 lb tarp system; 1 lb backpack; 2 lb quilt + pad system). And the rest of the system would have developed from there according to the principles of lightweight backpacking.
Instead, I carried too much weight for too long and spent too much money and time on heavy alternatives that I thought were essential or necessary. I do not regret it, but I wish my epiphany had come earlier.