Yeah, the amount of money sunk into just one gen watch used to (and still does, to an extent) bother me tremendously. I started out in the watch world with "affordable" gen watches then moved slowly to higher value pieces (some Breitlings, Omegas, etc) and just could not be comfortable with wearing and potentially damaging a $3000 watch.
Sold most of the gens and bought cheaper watches and reps. Still have quite a few gens but I enjoy a $300 rep just as much, and probably even more since I don't worry about them so much. The mid-range watch industry has gone mad and been successful to date, but I think a market correction is not too far away for them.