Being a bit older, I realised my taste continued to evolve. also my budget increased over time. With a few exceptions I only bought luxury brands, higher up the food chain, mostly Omegas. I almost only buy pre-owned full sets and mostly in online auctions meaning I rarely if ever overpay. Most but not all are popular iterations of e.g. a Moonwatch or various Seamaster versions, easy. I can flip any of my pieces (and do, currently have 3 for sale) and the key to making this hobby fun for a long time is being a good a price. The last 3 years I made money on every watch I sold, but it got harder this year and watches take time to sell. So in summary: think about what you want to buy and why, then buy at a good price. Right now it is turning into a a bit of a buyers market again so I am trying to liquidate pieces that are not essentially to my collection (mostly Tudor and vintage Omega Seamaster from 1950).