Don’t worry about value retention when it comes to watches, they almost all depreciate.

In my opinion, one of the highest quality ~36mm watches that you can get around $1,000 new is a Nomos Club. They can be had for around $1,250 grey market/asking dealer for discount. Definitely worth looking into the brand if you are not familiar with it.

34mm Junghans Max Bill (either automatic or hand winding) is another classic, German option in this price range. Will wear a little smaller than the Nomos.

Agreed with the other commenter. You have very versatile watches in just the three Seikos on the left. Stick to what you have, wait it out, and save up for one killer watch.

Honestly your best move (short of going to actually try on a watch) is to go get its exact dimensions and cut it out of paper to get a (very) basic sense of how it will wear.

I’m surprised that they didn’t give it tool less microadjust given the price, Longines is offering it on the new Hydroconquest GMT for less.