Thinking about selling something..

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@bsowers34, our 3861s have a lot of overlap (but I have the sapphire sandwhich 3861, not the hesalite).

Like you, I had the FOiS. However, I eventually parted with it due to legibility issues (beautiful dial though).

I have the white Speedy (wearing now), the Silver Snoopy, the sapphire sandwhich, and the reverse panda.

Get an EW321 if you want it (and I recall you mentioning your OB has offered), but for me (while I may consider one in the future), I would not want to part with any of my four 3861s for same. I realize others do not share this opinion, but I enjoy the variations. YMMV.

Good luck with your decision(s).
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Sell all the Speedmasters except one. You can only keep one. Keep the one that would make you the saddest to think of not having.

Maybe sell any others that you don't wear or aren't excited about.

Then wear your one speedmaster for at least six months. Don't buy anything. After then, if you still want a watch, enjoy the hunt.
 
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That's a lot of Speedmasters for sure. And then a similar style Tudor chronograph to boot. What is the rest of the collection like?
This is pretty much it, except for a few Invictas and a broken Eterna Porsche 911.
 
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To be a little more clear, I am not looking to fund another watch, I go through periods of what I call financial insecurity and sell stuff. I don't really need to though, it's more of a " I think I need some cash" thing.
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Sell all the Speedmasters except one. You can only keep one. Keep the one that would make you the saddest to think of not having.

Maybe sell any others that you don't wear or aren't excited about.

Then wear your one speedmaster for at least six months. Don't buy anything. After then, if you still want a watch, enjoy the hunt.
That one is the blue 3523.80. All of those new ones and it's still my favorite. Probably because one like it was my second Omega. A Connie just like this one was my first real watch purchase in 1987.