I'm an old head (41) and I worked in record stores and was a dj for a while so I copped most of my stuff from the store promos or record pools. I bought a lot of music, but rarely full price. Either at cost or $2-3 bucks. So a lot of stuff I never listened to.
When I got my 1st CD player, it cost around $400 IIRC. CD's were like $18 at the time. The first rap CD i think I ever had was NWA Straight...played it to def. One of best wax purchases was cutout of Nice and Smooth. Dope.
The only thing that comes to mind for something I spent money on....if any of you know of this....dont laugh.....Malcolm McLaren "Round The Outside". Riding off the Buffalo Gals fame they dropped World Famous Supreme Team. Wasnt feeling it...returned it to Starship Records.
The worst purchase that we actually kept...(although I think it was my brother that actually purchased it) was L.A. Dream Team. Yah....I know, ancient chit.