I owned a vintage 1965 Ferrari 330GT 2+2 for quite a while. I bought it used in about 1980 for $10,000 and watched the prices soar during the nineties. When my model was selling for around $100,000 I put it up for sale. Turns out this was the exact time that the used Ferrari market was crashing. I followed it down, lowering my price month after month down to $50,000 and never sold it. About 15 years later I ended up selling it for $15,000. Yes, it could happen to Rolexes and all the old mechanical watches when they go out of style once again.