Best Man gift seeking advice

[noxious]

Hello all, first time poster here. I joined this forum as I am trying to familiraize myself with all of the rolex options and I am a bit overwhelmed. I am not a watch collector but my best man is and I have decided that I will be purchasing a rolex as a gift of my appreciation. His collection is full of Omega and other brands that I am not familiar with, along with one Rolex Daytona (no idea of reference number). My budget is in the 7500 range but for the right watch I might go a little higher. The watches I am considering at this point are all SS models and listed below. He mentioned once that he rarely wears his Rolex because its a Rolex. I want to get him a watch that he won't shy away from wearing as much as he would like, something that isn't too dressy that he can wear to work or out to dinner with his wife.

1. Datejust II blue dial with sticks
2. Milgauss either black or blue
3. Sub no date ceramic
4. Sub Hulk

I like the date feature on a watch so I lean toward the Datejust or Hulk (a little outside of my range). My fear with the Milgauss is he may not wear it much because he would be worried about keeping it nice. As for the Sub no date that would be the watch I would buy for myself.

A little about the best man, sporty guy late 30's and director of a very large company, very humble and extremely generous. Doesn't wear a suit unless its a funeral or wedding, likes muscle cars and fine european cars. Just a general guys guy.

Thanks in advance for any advice.

Oh one more thing. Im not apposed to grey market but watch has to be brand new so any advice on good people to work with is welcome.