2 different answers here:

1.) cheap-ish watches such as seikos, micro brands, etc, just to try to scratch an itch, meanwhile in the end I lost money trying to sell these watches and could’ve saved the money and bought a nice watch I really wanted (obviously there will be cheap watches you want as well, I’m talking impulse buying here)

2.) I don’t really regret any nicer watch purchases I’ve made, part of the hobby that makes it fun for me is working within my budget and buying/selling/trading pieces to find what I like and what I don’t. Ive been surprised to find I didn’t like some watches on wrist that I loved in pictures, and Vice versa. You’ll always have regrets along the way and never really be satisfied, it’s a part of this hobby, so just enjoy it!:)