Gen Rolex used watches hold their value. I bought a gen used GMT 2C in 2009 & sold it the same year for same price. $5,200 with box & papers.
Reason I sold it was the green GMT hand & date. Thing is, if I would have kept the watch, I could have sold it 4 years later for over 6k & a profit, thanks to Rolexes price increase.
The gen that has been out if my grasp is the 18kt solid gold GMT, I had the money in 2010 & could have bought a used one with papers for 13k & now they are up to 15 or 16k.
I'm saving up for one as I've had several reps & gens & it seems that none hold true to their resale value in the rep world & gen world like Rolex.
Only thing with a gen watch, I tend to baby them meaning I don't beat them.up like a rep, bumping into things, etc.
Like mentioned above by another poster, I also know people that say I will never spend more than $100 for a watch, what's the purpose but these same people are living in a 300k house & drive nice cars.
Everyone has different taste. My cousin drives a BMW M5, expensive car but won't spend more than $200 on a watch, where I have a friend that drives a jeep & owns 3 gen Rolex watches, a SS Daytona, a 50th aniv Sub & a SS sub. He loves watches like me & could care less about driving an $80k car.
To each their own.