I'm a vintage Seiko fan myself. Good quality, most models are tough/rugged, interesting models and history, cost $150-$350, a fair number of customization options with aftermarket dials and hands. The divers are my favorites. Here is a quick intro to the current models
A WatchFreeks guide to currently popular Seiko Divers - Seiko - Watch Brand Forums - Watch Freeks
I like the SBBN professional divers and the vintage cushion case models, what I wear is a SKX007 that was re-lumed by IWW, nowadays I think they focus on customizing rather than mere servicing.
Industrial Watch Works | Vintage and Modern Watch Repair and Modification
I used to read this forum and it is a good place to buy a vintage or new Seiko and to become a WIS (watch idiot savant)
http://www.thewatchsite.com/
Speaking of WIS, here is one who's written some interesting reviews
Watch Reviews
You being a guy likely to use a watch pretty hard, hunting and tunneling and running and so on, you might get into the military watch subculture too. A good place to start is Howard Marx' shop
Home of WestCoasTime
I've bought watch tools and bands and springbars from him, never a watch yet.
I used to be pretty into watches, not expensive ones but still pretty interesting ones. That sort of culminated in getting and building one of these
uWatch - A DIY Programmable Scientific Calculator Watch
But it was not waterproof at all and ultimately proved too hard to use daily. It turned out that I didn't really need to do matrix math on my wrist.
Nowadays if I was going to spend $ on a watch, it would probably be something by Suunto
Suunto Core All Black | Outdoor Watches Sport Watches | Body Basics Fitness Equipment in Omaha, Nebraska
or Garmin
Garmin | Forerunner® 910XT
or this if it ever gets off the ground
Hands on with the new Leikr GPS sports watch | DC Rainmaker
Would I spend $$ or $$$ for a watch? Sure, if I had $$$ in abundance and I'd bought all the other toys I wanted, I'd get a drawerful of vintage Heuers and the winders to keep them ticking . . but it is my opinion that when you get into mechanical watches, for your $2,000 you are basically getting a name, snob appeal, male jewelry, and yes high craftsmanship but of a sort that doesn't really make any functional difference. That precision Swiss movement with the beautifully embellished gears and springs, in the polished case with the perfectly knurled pushers, might - just might - lose or gain 4 seconds a day. Actually, it probably won't even do that, that is COSC certification level. How impressed are you that your watch is wrong by only 4 seconds a day? Uh huh. Like I said, the $2,000 is getting you jewelry. Once upon a time, you would have gotten an exquisitely engraved small-sword or maybe a Faberge egg. Today, the male personal luxury object is an expensive watch.
That's why I'm more into functional watches - divers, militaries, sports instruments, etc.