The new Seiko SRPG field watch I think works great (although slightly more than your $150 range), but if your budget can stretch, I would recommend the Hamilton Khaki King II or Khaki Field. Those are a great one and done type watch
I use to buy a lot of lower / moderately priced watches eg Hamiltons, Seikos, C-Wards, Casios etc… about 1 per month on average, then it moved to 1 every 6+ months when I went up market ie Tudor, but after two big Rolex buys I’ve stopped buying. Still very much into the hobby, but getting a watch I love / wear daily (Explorer 214270 MKII), and frankly I overpaid for has taken some of the edge off. I still am on the hunt (looking for a Bruce Wayne) but happy to do that at a more reasonable pace.
It does matter, but not as much as it use to. Still important though if you intend to flip down the road, question is…is it just box and papers or do folks also care about hang tags, dongles and residual stickers?
I use to think that the waitlists were all fake and that all the ADs were selling to friends and/or out the back door, but I went to a Rolex AD, absolutely no history whatsoever (they sell only Rolex), told them i would love an Airking or OP41. I left thinking nothing of it, having registered my interest elsewhere as well to no result. But after 3.5 months I got a call and got my Airking.
I could not tell you why they decided to sell to me, I did not say anything remarkable or particularly funny / memorable. I did say I was not a flipper and that this was to be my first Rolex, I was wearing a Tudor GMT at the time, but besides that no idea why I got the call.
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