Personally I don’t hesitate to keep cheaper ones that aren’t worth reselling and don’t cost much to maintain. Basically any quartz that I remotely like, and any automatic where it’s cheaper for me to swap the movement than have a watchmaker service.

You could do something similar to what they recommend for wardrobe trimming, ie turn the hangar around backwards and turn it right ways over your wear that item then donate anything you haven’t worn at the end of the season. Helps drive home what your aren’t really using.

If you were going to trim, do it hard and fast, get it down to three: a dress (Quartz Citizen is my choice), a steel sports watch (sounds like SSK is your go to), and a GShock (whichever you wear more often).

Seiko Turtle SRPE93 has been next on my list for a while. Grey market price hovers about $375 USD.

Depending on your wrist size and your preference for quartz versus automatic, either a Casio MDV-106 “Duro”, or an Invicta 8926OB. Either way you’ve got a little bit of cash left to get a decent Bond style NATO strap.