This one has roped me in 😊 Don’t apply logic, I won’t be able to provide any either 😄

https://www.jaeger-lecoultre.com/ww/en/watches/jaeger-lecoultre-plrs/jaeger-lecoultre-plrs-chronograph-wt/905T480.html

Mine in order of preference

1. Time with hours and minutes- seconds are nice but not required
2. Chronograph that can run continuously  - vertical clutch and column wheel 
3. Date, preferably at 6 o’clock 
4. World time

Hope this helps 😊

I am probably in the minority, but Rolex is not for me. Zenith no doubt. Chronograph Sport with white dial and blue strap would be the ultimate sunny/summer day watch :)

Especially in 42mm with the cut off 3. Don`t ask me to explain why - I just do 😀

Excellent! I like IWC and in my experience the movements are really good. Great watch, wish I could pull it off, too. Aiming for the 43mm :)

I think you should pick a dress watch with a silver dial. It would nicely extend your collection. Any metal you like. Steel would be great and more versatile than gold. 

JLC Master Control and IWC Portugieser would give you choice of sizes and styles, and you would maintain focus on your hobby and collection. Rolex and Omega are “too obvious” in my opinion 😀 JLC and IWC are easily available, too

If the pictures are representative I would go for something with Arabic numerals. I feel they are forward looking, while markings are more contemplating looking backwards in time. You certainly must have plans for the future, and your next watch could be that turn in trajectory for you and your watches :)