I hear you. I feel like I have "settled" for some of the watches in my collection either because I was impatient and naive about watches or I did not have the money I needed for a mature decision, which is stupid because if I had been patient and saved the money I could have purchased higher caliber watches. I guess it's "live and learn". I am now planning on upgrading the watches I have by flipping them and replacing them with a higher tier.That's awesome! I think that makes me ~10 years older than you. I had a similar trajectory, having to wait until it wasn't financially irresponsible to buy the kinds of watches I really like and admire.
One of my hard-earned lessons has been to be really selective about what I want and what I don't. It was a lot of fun going through different watches and arriving at what I think are mature tastes (not mature as in grown-up, but mature as in I've had time for my personal tastes and priorities to become clearer to me). Now that I've done that, I'm over flipping and I'm really selective about new additions.
Question (and maybe this is another thread): Do you keep a list of watches and add to it as you see something you like or purchase a watch as you see fit? (Here's mine, I have not updated it for a couple of months, there are a few I would change/update)