Recommendations-1st Rolex

[jetdriver21]

First, a little about me and my lifestyle

I live in Colorado and am very active outdoors. I travel internationally 4-6 times per year for my job. I am a former pilot in the Air Force.

My current watches:
Omega Speedmaster Professional (hesalite, manual) the classic
Tag Heuer Link Calibre S

I am considering my first Rolex and after a cruise through the Rolex site and this forum have tentatively narrowed my search to:

GMT Master - Steel vs. Explorer II - Steel (White face)

My thinking is that both watches are very elegant. The GMT would be practical for my travel but I have read it is easier to scratch the bracelet and may be too much bling for some tastes.

The Explorer gets very high ratings as well, particularly the Polar Exp. I like this one because it would be different than my other two with its white face. It has a very simple, but effective look.

I have not had time to research pricing so any tips as to the going rate on both of these watches (retail vs. what i should pay).

Should I only consider new watches or does anyone feel the resale market might be the way to go?

Are there any other watches that I might have missed the boat by not considering? I am open to all suggestions and thank those who respond for their opinions.