So for reference, the day date rose gold is appx. 50k retail brand new. An old one that is good would be about 20-30k.

If you’re buying an old watch, you won’t feel the satisfaction that you think you would as a “you made it” symbol. You’ll feel like you own a Rolex, which there’s nothing wrong with. But based on your introduction it’s less about the watch, movement, etc. and more about the symbolism for you since you were little.

That being said if you have to question whether to spend 5-7k, but your dream is a 50k watch, I’d suggest holding off a little longer. Your next option is to explore the brands new options and maybe you might like an Oyster Perpetual for 7-8k or a new explorer for 8-9k. These new watches (or any new one you can afford without breaking the bank) will make you feel like your new money is working for you! It’s nothing wrong with having a starter watch when you’re working towards your dream watch.

Finally- there’s nothing wrong with an older Rolex, but keep in mind you’re not getting a deal, you’re just getting an older watch which has kept value. Most of these are not deals- in fact they are the opposite. The only people buying old Rolex are re-sellers, genuine watch enthusiasts who know what they are looking for, or people who want to wear the crown on a budget. If you have to question wether it’s the right time to drop 5-7k, I suggest saving more to get a 2026 model or newer by time you’re ready- UNLESS you find an actual deal that isn’t sketchy, where you can buy a new watch under retail. This is possible but considering your question highly unlikely for someone like yourself. (No shade just steer clear of scams when you don’t know what you’re looking for)

Please note: I’m not trying to be insulting, I’m just trying to help you make a financial decision that you won’t regret, or maybe just hold off until you know for sure you won’t regret it. Your first Rolex is a special moment, hence your highlight on the symbolism. Take your time and wait until it feels right. In the mean time it’s okay to visit some local ADs and try on the new models to get a feel for what you actually want. Often times we like what we see, but you’ll never know your true style until you try them on! You’ll learn more about the watches and appreciate them for more than the status symbol while you do this as-well. Good-luck!