Up until now the most I have ever paid for a watch was $150 for my Luminox (on right) - mostly because I tend to break watches within a year. The Luminox has been seemingly indestructible now for over 4 years though and the sapphire crystal doesn't even have a scratch.
The one in the middle is my new Lum-Tec Combat B1. I saw it in the pictures below and couldn't get it out of my head. I couldn't pull the trigger at $595, but I saw that a guy had them on ebay and was accepting offers. I offered $500 and he took it. It looks like he still has a few left if anyone is interested.
It seems like a great watch so far, and I get complements constantly.
The other watch in the top picture is just a Citizen Eco-Drive chrono. It has been a good watch, and I picked it up fairly cheap, but the crystal is plain mineral glass and is already scratched pretty good. The cool thing about it is that it is solar powered.
The other watch that I can't get out of my head is the Ollech & Wajs Mirage II (the Mirage III ain't bad either). Fucking gorgeous. They seem a little hard to come by though.