Hey guys. Help needed on my first Omega purchase - a Speedmaster

[tough]

Hey guys, hope you are all doing well.
I have to start by saying that I am relatively new in the watch world.

I have currently a Rolex SS Sub, and a Patek Aquanaut.
Both watches that I enjoy and wear a lot.

After much consideration, and lurking around, I want to add more complications to my collection over the years, and I would love to start with a Chrono.
At first I was thinking of a Daytona. In all honesty, I didn't fall in love with it as much as others have, it just didn't sing to me as much.

Then I cam across the speed master. I absolutely love the history of that piece. Omega brings more diversity to my collection which I also like.
I just see so many different versions, and am a little lost on which ones are the more admired ones.
How does one pick from so many different versions.

Are the numbered edition special?
I have recently seen one on a leather strap.

Appreciate your help and thank you!