I did this to some extent a couple of years ago (probably at a lower level than you might be thinking) and ended up selling it and going back to a scattering of cheaper watches.
Trouble for me is I can’t ‘really’ afford an expensive watch, and by afford I mean afford to lose it, damage it or for it to depreciate to nothing. It was this special thing (great in some ways) but meant I didn’t wear it much and if I did was worried I’d damage it. Before I knew it I was wearing cheaper watches all the time and it just seemed pointless.
I did also realise I get a lot of pleasure from messing about with many, even choosing what to wear and having different watches for different occasions. I also realised that cost doesn’t equal instant happiness and I’d personally rate my 6105-8009/Seiko bullhead/silver pogue way more interesting on the wrist than anything in the current Rolex or Tudor line up.
Until Tudor bring out a submariner I’m unlikely to be tempted to do it again.
It’s a bit like watching the recent car pervert Chris Harris interview when you realise someone like Chris gets more pleasure from old Peugeot 205’s than a modern Ferrari. We all think we want/need better but sometimes it takes that taste of caviar to realise you prefer fish n chips.