Ha, great timing: An hour ago I set a reminder for myself to play each of my six pins for 30 minutes today to confirm which one or two I might let go. I've never had six, and I'm getting a hunch that it's one or two too many for my comfort - I'm generally a "less is more" kinda guy. I'll know more this evening!
And to directly answer the question, yes. Often. I often think about money, and what things are worth, and are they depreciating, etc. I sold my two year old VW GTI because I wasn't driving much and it (was) depreciating too much. I got an old Mazda minivan for cheap, and now I have a pin hauler as a bonus! I look at my pins and think "Is it crazy to have $45k in pins?" and I think the answer is a firm maybe, but as long as prices stay steady I'm content-ish. I think it's a bit crazier that the average pinhead that I've surveyed has way more than this!