1. Limited units available
2. Beautiful design or feature.
3. Sophisticated movement
4. That Watch will not be produced as a retro version as new anymore.
5. Timing (factors like Trend, preference on colour, size, material) *
If you said buying a new Rolex and put it in safe waiting for the price to go up and earn money, that may not be practical, as they are production watch, and those are new, you may have to wait for many decades to see that watch could offset inflation to return you some dollars.
Simply as I say No Rolex should be purchased with a perceived notion of investment....
They should be worn and enjoyed! Or more precisely having said that, almost all Rolex watches will hold their value in the long haul, but will loose out in the short term.
Watches should not be bought as an investment. Buy the one you like and enjoy it. If it goes up in value that's great!
If buying with the sole reason not to loose money on a future resale then buy second hand as most of the depreciation would already have been taken.
Your best bet to buy a Pre Owned Submariner, GMT or SS Daytona. They seem to hold their value pretty good in the used market.
I bought a 1950 bubble gold 14K Rolex in 1986 at HKD$5,000 from Kiu Tai Yu. After using it for almost 8 years and then I sold to some one with HKD$18,000 … and that watch price kept going up to HKD$38,000 in 1996. but due to the trend for watch size was going BIG, that Bubble back Rolex was not able to further appreciate much after 1997.
If I were you, at age over 38. I have no hesitation to recommend you to buy a used Day Date Ref. 18038 (Rolex Flag ship model). For your daily uses,
This is one that has its own specialty, the dial is beautiful, even colour, brown orange colour that is eye-catching even from a distance, Sapphire crystal for scratch proof, watch proof is not a question for Rolex, Day date is best for man like I to remind me the important of the day and time. Perpetual Auto rotor keeps power reserve for min. 42 hours. Price, estimated to be HKD$44,000…and I am sure the price will move up with inflation.
It is not an investment item, but after 10 years, you may able to get back at least HKD$35,200. So it costs you HKD$9.6 a day to own this watch.
If you don’t like Day Date, simply go for s used Submariner, GMT Master I or II.
Talking about real investment, we have better go to buy some blue chip when Hang Seng Index goes down to 18,000 points.
Note * a very ugly colour like Mandarin Yellow or Stella (Red) in the 60's which no one wanted, and was made only a few units... now it is likely to be very rare and expensive.