I think in terms of overall desirability of Rolex Sport watches in descending order are as follows (subjective of course). It is also no surprise that the price follows this ranking.
1) Daytona
2) GMT Master
3) Submariner Date
4) Submariner No Date
5) Explorer
6) Milgauss
7) Air King
However, it really depends on what you are after. A lot of Rolex enthusiasts will argue that a simpler, more understated Rolex sports watch like the 114270 Explorer 1, or pre-ceramic Sub 14060 are also highly desirable.
I guess it depends on how much you want to 'display' that you are wearing a Rolex. If you belong in this group, stick to the top 3 mentioned above.
PS: You may even want to consider a Oyster Perpetual 39 - not a sports Rolex, but still a Rolex nonetheless