Not a fan of the vintage models and subs myself, though I love, love, love the look and feel of my DSSD. I even have the incorrect 10 date spacing on the V5 ult. and it just adds to the charm.
Now about the older Rolex, my buddy has a gen sub from the 70's though I don't like the feel of the bracelet (feels thin and cheap) and find the watch wears a little small.
When people see the DSSD there are mixed comments. I wear it on a zulu bond and some girls have asked if it's a fake because of the nylon strap etc. I just tell them it's much more comfortable than the SS bracelet in the summer.
I did have another friend comment on the DSSD and say, hey Rolex finally got it, they started making proper sized watches. Then again, he wears a briet and it wears small on his wrist.