Chief-Rick - as other posters have stated, you can definitely go down the rabbit hole on this, but it's a fun journey. If you end up going the high end route (Rolex, Sinn, Panerai, Omega Speedmaster, Tag, etc.) you might consider used. Depending on make, model and condition you can save 40-60% off of new. Some brands tend to go in and out of fashion. Panerai was very hot about 10 years ago - now not so much. (And before anyone jumps on me, I own a Panerai and still like it.) Same thing for Kobold. Used to get a lot of attention, but you don't seem to see much about them any more.
If you really want to have some fun, try reading old watch snob articles (sorry I don't have the link). But keep in mind he really is a snob and kind of a tool.