The watch before your first Rolex?

[Chadridv]

So a dear friend of mine has a strong mind for collecting and is perfectly suited for watch culture. I just talked to him about the Patrizzi dial Daytonas and he was completely fascinated and inspired by the idea of imperfection leading to rarity and value.

That's just to give you an idea of my friend.

So, he's interested in buying a rolex, specifically a Pepsi bezel GMT. Likely a modern piece but perhaps a tritium dial so 80s or 90s.

Being he doesn't even own 1 watch, he's apprehensive about making the purchase. I try to avoid the word "investment" with him but in the big picture I try to explain to him, you are investing in collecting something that will bring you joy, continuous enthusiasm and hopefully will appreciate in the long term.

With all that said, he's starting to consider an entry level watch that he can wear daily, comfortably and that won't break the bank. He really likes the idea of a vintage-ish rolex, and I'm thinking he could probably make his way into a micro brand (steinhart, OWC, etc.)

I've decided to post this in the Rolex section because I really want the opinions of Rolex owners who have experience with affordable brands, either before purchasing their Rolex(s), or who continue to do so.

What would you guys suggest for a first piece pre-rolex to get his feet wet? Hopefully Around the $500-$1000 mark.

Thank you!