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It's a gamble in that you need to know what you are looking at, to avoid buying a turkey. But, all it takes is studying some photos and you can become sure about what you are buying. I always pay close attention to dials and hands as they are often replaced and swapped out. If you get movement shots then generally I just look out for parts that are tarnished differently from the rest of the movement (can suggest it's cobbled together) and also note if the regulator arm is way off centre, if it has one. People often sell watches as "running strongly" or "keeping great time" whereas in fact they are as dry as a bone and dirty. For ones which I wear regularly, I make sure they get cleaned and oiled, so factor in say £60 - £100 to have that done.
Gamble how? Purely based on whether they're in good condition or not? The 53 fat arrows and the Hamilton 6B are really nice.