My two cents… having gone through this too:
Define what style you want - there are so many references, it’s really overwhelming. Take your time, browse freely and write down references you like, then start to go deeper on these. The styles (dials, cases, movements etc.) were different in the 40s than in the 50s and 60s and so on. This forum has incredible resources and threads summarising everything you need to know on various refs. Gaining that knowledge on specific refs will give you more confidence and comparison points when you spot the watch that could be yours
Understand what you want - a watch for daily wear, a watch for special occasions? Automatic? Quartz? Vintage or not? Few watches but pristine state? Or plenty of different watches with some wear? What’s your tolerance for being original? It’s easy to go crazy, there are so many nice watches out there. But it’s relatively expensive especially if you start to factor in services. So depends on your budget, but also on how much time you really want to spend searching for them. This is the funniest part for most, but a constraint for others. There are always options to reduce that time, like paying a premium and getting it from specialised vendors who buy/service them - no harm in that either!