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I tend to go through my wants about once every week or two in an attempt to shorten my wants list. I started out with 30+ pages of wants and I've managed to cut it down to 9 pages. There were tons of pins that make me go "Why the heck is this even on here!?" and then wonder if maybe I randomly add pins to my list while I'm asleep or something, lol.
In the early years, a lot. Most of what I removed were things I never thought I had a chance at actually getting. Then after I got back into trading when DPF started, I cut it way down 300-400 pins, and kept it that small for about a year, so I could focus on cleaning up a lot of sets that I had started collecting years ago. After that year, I've been building it back up and now it's just over 1100. I don't foresee removing that much because I know they are all things I want to collect, and I added things one set of pins at a time. There is a small group of stuff I might remove, mostly UK pins because I wanted to have some wants that overseas traders would have. But with as popular as the UK pins are now, and since they stopped doing Core pins, I think they're now "stuff I'll never get."
I remove them whenever I hopefully get them. Until then it reminds me of whats out there and what I would eventually like to add to my collection. Even though I know it is very unlikely that I will get some of them. But I think it definitely doesn't hurt to have a lot of wants. I always looked at it as the more wants you have the more possible trade requests you may receive. My problem is more along the lines of I could use some more desirable traders.