First off, I just buy what I like, I'm not much of a watch connesiuer (sp?) so don't take my opinion too seriously. As many in this thread have pointed out, there are probably other watches with better pedigrees in the same price range. IWC is really nice, I want one eventually.
When I bought my Breitling, I had heard that they are very, very strict when it comes to buying from an authorized dealer. Since the Breitling was to be my first "good" watch, I didn't want to screw around and buy off the grey market or off Ebay. I ended up paying full price (minus a 15% discount for signing up for a Macy's card) at Macy's Jewel Gallery - I paid $2,550 for the watch and bracelet. So, to answer your question (sort of), if you can get the watch through an authorized dealer for less than $2,500, you are doing OK. A quick check of Ebay shows the watch going for $2,200 - $2,300, so I guess you can't expect much of a discount. As a side note, our local Costco had some just like mine a little while ago for $2,300 - not much of a discount, but I assume that Costco was acting as an authorized Breitling agent.
As for other suggestions, again, I am no watch expert so I only know what I like. The only other watch that was in the running when I bought my Breitling was the TAG Aquagraph 2000 and as I mentioned above, I picked one up last week. TAG seems to be a little less fussy about where you buy your watch, as long as the serial numbers are in place. That's reflected in the going prices, I almost paid full price for the Aquagraph ($2,750, yikes!), but I found a new one on Ebay for $1,500 shipped, which, upon checking other auctions, doesn't appear to be an unusually low price.
If you are like me, and you will probably never really get "into" watches, you just want one, maybe two good watches to wear all the time, then buy what you like. Since it will be a user not a collectible, then its future value is somewhat of a moot point.
A funny side note: a little while ago, when I first got my Breitling, I started buying and reading a couple of those high-end watch magazines that you can find at Borders. I would just flip through them, and drool over the watches that I could never afford (wristwatch porn

). Well, in one issue, the magazine presented the results of an earlier survey, one that was done to determine what the average reader is like. I remember that it said something about "... you own 9 high end watches, your annual income is just over $1 million..." Apparently, I'm in WAY over my head!
