Brand new 1989 Sims Freestyle. Man, I saved my allowance for a year to be able to afford it 50/50 with my brother. I was 9 years old... Sorry, no pics and like-board pics from the web don't seem to work for some reason.
My first deck was an Original Sin 155cm, I forget the name of the model. Paired with Burton Customs and Vans Lemmings, that setup was my entire world - I was the kid at school who actually owned a setup, rather than having to rent.
Man, I really liked that deck - I progressed quite a bit on it, on family trips to Utah and Colorado when I was a kid.
I think from now on I am just going to keep every deck I buy, and stop reselling unless I really really hate the board.