i grew up on 7.75 until one day when i walked into a shop in the city i had just moved to and was like, "where are your 7.75s" and they didn't exactly laugh at me or anything, but you could tell it was just not a thing anymore, so I moved up to an 8. I skated them for a few years, and then I kept noticing whenever I'd see pros talking about their boards that they seemed to be on 8.125s, so I decided to try that and got used to it. then i fell on hard times and had run out of old boards to skate, but had always owned an 8.5 setup for this fantasy of skating vert (never really worked out) so I rode that and enjoyed it but it was definitely too big for me, just hard work, but nice to have so much room - so then when i finally could buy shit again i got an 8.25 and some 149s and it's kind of perfect (for me obviously).
i think i'll always have a nostalgic niggling about maybe getting a smaller setup again, but i think i've found my goldilocks board.