The watch you can actually buy, at the price you actually have
r/Watches keeps a buying guide: one thread per price bracket, one watch per comment, ranked by the people who own them. It is an excellent list and a wall of text. This is the same list with the watches in front of you — sortable by price, case size or how many people backed it, and filterable by style and movement.
$500 – $1,000
Seiko, Mido, Junghans, a used Sinn. The widest spread of good answers anywhere in the guide.
$1,000 – $2,000
Sinn, Tudor, NOMOS, a smaller Speedmaster. The bracket where the specs stop being a compromise.
$2,000 – $5,000
The Moonwatch, a vintage Datejust, a titanium Pelagos, two Jaeger-LeCoultres.
$5,000 – $10,000
A Grand Seiko Snowflake, two Submariners, and a moon phase you can read across a room.
The rest
$0–250, $250–500 and $10,000+ are next, pulled from the same set of threads.
In progressPhotos are sourced from retailer and manufacturer listings for identification only; prices are as quoted in the original threads (2020 for the $500–$1,000 and $1,000–$2,000 lists, 2017 for $2,000–$5,000 and $5,000–$10,000) and will have moved since. Links go to the source given by the person who recommended the watch. Original threads: r/Watches buying guide wiki.