I struggle with this as well. I feel that if I purchased a higher end piece (ex. any standard rolex model) that I would feel added pressure to wear it all the time and thus not enjoy my many other pieces. Also, I feel that if I dropped 5+K on a watch that I would become hypercritical of any small flaw that I noticed or any amount of poor fit or wrist rub. Ultimately, I feel that watches should be fun. They bring me joy. So, I have accepted that I don’t care if I have 10 or 100. The fact that we are on Watch Crunch likely means that we are not likely to be a one watch person 😃