You mentioned having disposable income to try a lot of gear to see if it fits your needs. I think there's a definite relationship between experience and gear (and I'm coming from a range of positions, from having to buy what I could afford when I had kids at home and was just getting established in a career, to being able to tinker with my outfit to my heart's content now that the kids are self-sufficient, the house is paid for, and the career well-established.)

In the early years, cost was the major factor controlling my camping life. I would go out for a few days, determine how everything worked and gain the experience to make do with what I had, and then prioritize what I wanted to replace (thereby answering the incessant, "What does Glenn want for his birthday/Father's Day/Christmas?") Experience colored my gear selections heavily: the American Camper e-frame pack worked, but was never really comfortable and needed constant repair; it went high on the priority list because no amount of experience can overcome an uncomfortable pack. However, I learned how to deal with bugs and rain because all I had was a tarp. I learned how to prepare simple meals, mostly based on ramen noodles plus "mix-ins" because all my Sterno stove could do was boil water. (I still remember the glorious Christmas when I unwrapped a Svea stove!)

As time went on, the role of experience gave way to gear selection as a major focus. Partly, this was a function of reaching the "five years experience four times" feature of spending 20 years hiking in Ohio, Kentucky, and Indiana forests - not a lot of significant experience remained to be gotten, so you spent 15 years refining and repeating what you learned the first 5 years. Luckily, this shift in emphasis coincided with a shift in disposable income.

However, the experience gained had a major bearing in how I selected replacement gear. First, I went through a light-at-all-costs phase, reducing basic pack weight to about 8 - 10 pounds. What I found was that this gear was usable, but was near the lower limits of what my experience found to be comfortable. My own experience was that I had learned to get by with whatever gear I had, but that the best trips featured, first, gear that faded into the background and, second, a light pack. I had the light pack, but the gear needed constant fiddling with - it wasn't fading into the background. As a result, it detracted from the trip rather than adding to it (much the same could be said for the early years' gear, too.) So, I fiddled some more, threw some more money at the problem, and finally came up with a set of gear that I can use almost without thinking, and my trips were now more pleasurable while the pack remained at about 12 or 13 pounds base weight.

However, gear never replaces experience. Instead, your experience establishes your unique set of preferences and needs, and drives your gear selection in that direction. The gear should remain a means, not an end. (By the way, some of my discards fit others' experience-driven preferences very nicely - so it was a win-win for me.)