In my experience (over time) it really comes down to what watch/watches you TRULY like. I get the iconic thing, the resale thing, the value thing, the newest greatest thing etc...
But in the end I have found that I am personally drawn to a limited list of watches I TRULY like. Top of the list is my 16750 Polar Exp II , my 16710 GMT Master II and my classic Sub 16610. Throw my Speedy Pro in the mix and it's about perfect. I also love a couple of Rolex "Ceramics" (my 116710 & 114060). Then the list gets a bit thin. Each of us has a different list!
To me personally it's about the journey. I have been very fortunate to own IWC, more than a few Rolex, Omega, Tag Heuer, JLC, Girard Perregaux and many other brands to name a few. God knows how many actual watches. But always enjoying the pursuit & the new watch experience.
Now having said that... I am TRULY frightened to dip my toe in the awesome Patek Philipe water. I have no doubt there will be no turning back and my checkbook and wife may not be able to handle it.
I am pretty sure that day will come regardless of whether or not I have anything to do with it. Patek will win... and more than a few of my current collection will lose.
Of course there will always be a few Rolex in the mix - that way the planets will still align and the the sun will still rise
Give me strength