What are you viewing things as? What matters to you?
Is it the design? The strap/bracelet? The weight? The movement? The specs? The history behind the brand?
I've got quite a few watches at the Sub-$1K price point and there's different things i like about each one, for example, this is what I like about 3 of mine:
1 - Vostok Amphibia. I love the engineering of it. I love the Soviet/Russian approach to problem solving, while the Swiss divers of the time were putting chunky crown-guards on their dive watches to make sure that the crown and stem wouldn't be damaged, they instead changed the crown so it had to be pulled to engage to do the same job with less material needed. I love the acrylic crystal specially designed to become more waterproof as the watch goes deeper. I love the history behind it, that it was a legit "space watch" (worn into space in Soyuz-17 for example).
2 - Swatch. I love the /fun/ behind Swatches. I love the retro charm of the 80s styled ones. No, they're not going to win any awards for the best specs or best value of the money, but they're fun to wear every now and then.
3 - Vintage Smiths. I love the history behind the brand and them beating Rolex to the top of Everest. Its fun to wear a watch made in England, once one of the horological capitals of the world and contributing some of the key enhancements of watches.