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.