I totally remember that feeling! When I first started hunting for 60s divers, being paranoid about overpaying was my baseline. Using specific data tools makes everything so much clearer. Personally, I use an Etsy price monitor to track prices on those smaller platforms where you find the best deals. It's fantastic for spotting when a brand is starting to trend before the prices actually skyrocket! Just stick to the data.

Honestly, if you want to avoid that spinning head feeling, you gotta stop looking at individual listings and start looking at the aggregate data. The watch market moves like any other commodity, but vintage is way more volatile because condition is basically everything. A 1950s Omega can be 400 bucks or 1400 bucks based solely on whether the dial is original or the movement was serviced by a butcher. I usually spend my time looking at price history charts on dedicated aggregator sites to get a feel for the baseline. It helps you distinguish between the actual market price and some random guys asking price. To keep track of specific pieces I am hunting across different sellers, I just use PriceDropCatch to monitor my favorites list and send me alerts when things actually hit my price point. It is way easier than checking manually every day and it stops me from panic-buying when I see a fake deal. Since your budget is 500, you are mostly looking at entry-level vintage stuff like Tissot, Longines, or some smaller Omega models. Stick to pieces with clear movement photos so you can verify the caliber numbers yourself. If a seller wont show the movement, just walk away. Also, ngl, recently serviced is usually a lie unless they have a paper receipt from a real watchmaker. Tracking those technical specs is really the only way to know if a price is actually fair or if you are just paying for a shiny case.

Welcome to the rabbit hole! Honestly, that 500 dollar range is a bit of a minefield tbh. You really gotta be careful because thats where most of the redialed or frankenwatches live. I always suggest checking sold listings on eBay rather than what people are asking... asking prices are usually just a fantasy. If you want that stock market vibe you mentioned, you should definitely check out WatchCharts since they aggregate data from all over. It helps you see if a model is actually trending up or just overpriced. Just remember that condition is everything with vintage. A beat-up Omega might look like a steal, but a service can cost more than the watch itself. I would suggest staying away from anyone claiming a watch is a guaranteed investment at this level. Just buy what looks cool on your wrist and do plenty of research before clicking buy.