Would you flip?

[Robbmill]

I appreciate the collective wisdom of this forum, and turn to you all again with a question. I am in a position where I want to make the collection a bit smaller. I have a few really nice watches, but seldom have the opportunity to wear them as I turn to my Explorer II and Tudor Black Bay Black most often.

Do you think it is a good idea to sell my IWC Pilot's Chrono, Omega Mark II, Oris Aquis Date and Ebel Tekton 1911 Chrono and replace it with a watch such as a Yachtmaster or GMT Master Black/Blue?

I figure in total I can get close to $7500 for the trade-ins and I would be willing to throw in a bit for a new Rolex.

This would leave my collection a bit more manageable:
Rolex Explorer II - Polar
Tudor Black Bay Black
Breitling Chronomat (huge sentimental value)
Breitling Super Avenger (huge sentimental value)
Hamilton Pan Europ

Thank you in advance for your advice/insight. I look forward to the responses!