Sales regrets or not?

[Oldngrey]

Hi all. I was wondering how many of you have sold a Omega or multiples of to fund a Rolex and if they now have any regrets?
I’m currently considering selling two Seamasters in favour of an Explorer which would be my first Rolex, but both have valid reasons not to. There’s my 2264 which I like for the comfort fit and the legibility of the sword style hands, which I find I can easily read with my ageing eyes.
Then there’s my current style diver 300 which if I’m honest I regret buying, and I don’t wear much plus I find it harder to read.This would be the obvious choice to move on, but I bought it when my first grandson was born and I said I would eventually leave it to him, so I’m torn on moving this one on because it’s basically his birth month watch, but will a watch that’s lived in its box for years mean anything to him? Or would he prefer a watch with a few scratches that his grandfather actually wore, because my intention is to make the Explorer may daily wearer and enjoy wearing it, and not worry about it.
Any thoughts or anyone done similar.
Thanks
Mark