@mosy that's such an open question, but...I never let an enabling opportunity slip by. I wouldn't go for the second option, because if you've got $2k for toys, it seems a shame to only ever have a $200 watch. Not that there's anything wrong with a $200 watch, or a $100 watch for that matter, but as you have the option to scale up, take it.
For $2k there are some incredible used options. Personally I've been ogling a mint Black Bay at about that price. But perhaps you can give us a little idea of who you are and what you like? Do you wear a suit and tie for work? Like straps or bracelets? What do you already have?
Thanks for the engaged response. So I don't usually have $2000 for "toys", but on occasion I do. But even when I do, I try not to use it on toys, but rather save save save. For whatever reason, I am presently willing to drop this amount on a watch or watches. Do keep in mind that if I went with option B, I would likely have one or two watches in the $500-650 range, meaning my top piece won't be $200 as you fear. Having said that, you're point is well taken.
Regarding used options, I'm concerned about the headache of making sure I'm getting a genuine piece. Don't want to do too much homework in that regard. So I definitely prefer new. However I can be convinced to go used.
Regarding me, most days I wear a blazer, dress slacks, and dress shirt, sometimes with a tie. I do wear suits to important meetings about once a week. Overall pretty conservative. I try to wear clothes that have a classic vibe, but with modern fits.
Until about six months ago I was going without a watch. I decided to try wearing one, as I noticed it added a lot to a person's overall appearance, especially up close, like in a meeting. What I also noticed was that from a slight distance away, I oftentimes couldn't tell if a watch was a $50 watch or a $15,000 one. And what was really interesting to me was that when I was closeup with someone, I would often see that it was a mid level employee that was wearing an expensive piece, and the executive was wearing sometime worth much less. So I decided to start with something on the lower end and see where that would lead me.
I knew I wanted an automatic and I settled on an Orient Bambino II, with white dial, dark blue hands, and dark brown alligator strap. I liked the look of the watch and I still do.
Now that I'm used to wearing a watch, I've decided that I'm willing to invest up to $2000 on either one watch or several cheaper (but good quality nonetheless) ones. So that's where I stand.
If I was to go with a single watch, I would most likely go with a leather strap and a light colored dial. I really like the Tag Heuer Carrera, but am very interested in hearing other ideas that are somewhat comparable.
If I went with several watches, I'd probably start with a Tissot Visodate, also with the light colored dial and leather strap, and then build from there. Perhaps a Seiko with a bracelet, maybe a Bulova chronograph, perhaps a black dial Bambino III. Open to suggestions here as well.
And just to get back to "used", if you can give me some fool proof guidance on how to make sure I don't get a fake time-piece, and lead me to some good value ideas, well, who knows, maybe I'll be convinced.
Everyone - feel free to weigh in!!
Edited by mosy - 5/1/16 at 10:18pm