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Horological Meandering

I guess you have gotten to Step1: Recognizing the problem.

 

Now, as for solutions, I have none. There is always another one, and another one. 

My way of dealing with this issue is to only buy a watch when there is a special occasion to mark it. That way, each watch is associated with a special moment/place/achievement. Of course, then I start making stuff up to justify something I want now.
The only real advice I can offer is to take your time with each. Make sure it is what you want. Make sure you can live with it for a while. Do not think about resale value, as that is nothing but a guess, so eliminate it from the equation. Only when you're certain about these should you pull the trigger.

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