I quit long ago, but loved skating. My boards were as follows (in order of ownership):
Zorlac Metallica Spider
Powell Peralta Mike McGill Skull & Snake
Santa Cruz Eric Dressen
H-Street Tony Magnusson
All those boards were made for half pipe - which is fine, if you had access to one. Ditch they were okay for, and street they were beasts. (The Metallica board was the worst, it was so front-heavy.)
The kids since the 90s have no strength, so they started making them more like freestyle boards, and skating upped the ante by getting rid of anything to do with using your hands.
That Santa Cruz is probably my favorite. Before the uni-boards came, that general design was the best all-around board. Good ollie tail. That Hosoi was pretty nice, too.
It seems to me that the era to collect from should be the one that most means something to you.
For me it was the 80's era, particularly from 86-89 (I stopped skating in 89). I remember when I stepped up from my Valterra (Back tot he Future) board to a Madrid- Bill Danforth.
This was my story, too - except my first real board was an Eddie Reategui. My friend had a Danforth he liked a lot.