I was like you before.. similar 3 choice and i choose to get my rolex datejust first.. and now i am thinking of a second watch and also was deciding between the chopard happy sport or cartier santos.
I would say the rolex is a classic piece... just like a chanel classic flap while the cartier/ chopard are more like seasonal reissue..
just a rolex first if this is gotta be your first watch.. at least the value is there..
if you don't already have a rolex, get the rolex first. Every watch collector needs a rolex! Then get chopard when you're ready for another watch. Their happy diamonds line is tdf!!