When do "you" know it is time to flip a watch?

[GRabens]

About a year ago I obtained what I thought would be my Grail watch. It was a 116613lb from one of the trusted sellers. I traded a 116520 Daytona black dial. The Daytona only lasted about a year. I also currently own a Breitling B1 and two Datejusts. I have owned the Datejusts and B1 the longest 5 years or so. Honestly, the 116613lb sits in my safe and I wear one of my Datejusts most of the time. As I type this, I probably have not worn the sub for about two weeks. I would like to add a Hublot to my collection. Moving the 116613lb would allow me two do this now. I realize this is a Rolex forum and this would probably not be a popular decision here. However, I am just not wearing The 116613lb. And I like the modern look, feel, and materials used by Hublot. Plus I feel like I could wear the Hublot and be more undercover then when I strap on one of my Rolex watches.

With that said, I still like the 116613lb but I don't feel like it is getting the attention it deserves as it is the most expensive piece in my collection. I lusted after the Daytona and sub for so long, that I think once I finally achieved acquiring them the thrill of ownership did not last too long. But at the rate that Rolex increases their prices I am afraid that if I left the sub go I will not be willing or able to pull the trigger again. Hence, the flippers dilemma !

I have flipped watches before. Sure I miss them, but I have yet to replace any models that I have moved on. Do I continue on my watch journey and flip to the next coveted model? Or do I hold on and wait until I can add another piece to my collection. I am also concerned about collecting too many watches that end up sitting in a safe instead of getting worn and appreciated on a regular basis. Not to mention the up keep costs associated with having to maintain a large collection of high-end watches. I will also add for your consideration that I am not a one watch guy. I like to have at least a few to interchange.

Any feedback or suggestions would be greatly appreciated.