I started in '88, when I was a very small child. The skateboard was massive and out of control, so I was thrilled when New School skating emerged and I could ride a somewhat appropriately sized deck.
I've always skated, but there were times where I took it more seriously, but I would say that I started again in earnest (meaning I started thinking about skating, cared about my setup, made time to skate during the week) about 5-6 years ago. Like every aging 30-something skater getting back into it, I thought I had to get a 9" wide board with Ace 66s or 159s Indys, so I did. It was fine and fun, and I'd still skate that setup today (all the parts are in a box in the basement), but then I started sizing down and realized that I skate much, much better on a "normal" width board.
I've been gradually slimming down, to 8.75", 8.5", and now I've found my sweet spot at 8.25" (give or take) with 144s, with a 14-14.25" wheelbase. I even set up an 8" popsicle, using some sweet Indy 139s I found at the thrift store, but I don't skate it much because I find the 8.25 to be so perfect for my needs. Anyway, I expect I'll stick in the 8-8.5" range from now on. It really works for me and I don't see a huge advantage to wider boards and trucks.
FWIW, size 9 shoe