I've always been into slight hot rod, but not quite a 1/4 of an inch - my timeline is as follows:
96' - first board 8" with 8" trucks - I was 11 with a size 7 shoe, could have gone smaller for sure
96'-99' - down to a 7.75" with my same 8" trucks, I was poor and legit skated my first set of indy's for 3 years (prob 4 decks, I remember having a new deal and a powell blank)
99'-00' - got on the 7.62" train with 7.75" trucks - thunders, and won some royals in a context - skated a lot of girls and AWS's - I learned a lot of flip tricks on this setup, I remember getting a wenning board in the first habitat drop and learned 360 flips, frontside flips, switch kickflips, and half cab kickflips in one weekend
00'-05' - got a shop sponsor and some distributor flow and landed on the setup that lasted through my best era of skating - 7.88" (almost always aws, habitat, girl, chocolate) on 8" destructos ... I know they get mad hate but at the time the mid height and crazy king pin clearance was perfect for me
became a full time touring musician around late 2005 and stopped skating as much
06'-2022' - randomly bought a board here and there and tried to skate but never got comfy - usually 8"-8.25"
2022 - 2023 - tried 8.5"s and 8.75"s, did okay on a 8.25" quasi proto for a min, but finally landed on 8.38" with 8.5" trucks, which is the same feel as my golden 7.88" with 8" trucks setup but half and inch bigger. Lots of tricks are coming back on this, I really need the slightly wider trucks to feel grounded I think. I'm 6'1" with size 11 shoes btw