Hey OP, do you have to put lots of stuffs in your car/trunk all the time? Or you like to do crazy grocery shopping?
Lots of ppl think the trunk space is a problem for the Z, but actually it is good enough for regular grocery shopping. Especially you are single, I wonder how much trunk space do you need from your car.
As for a DD, do you have heavy snow in Winter? I used to drive my 350z all year around even in Winter, as long as you put on a set of Good snow tires and drive carefully, you'll be fine in Winter, it's 70% depends on the driver, it's clearly like that when you see how many SUV jump into the ditch during snowstorm.
As for the ride/drive, I will put hands down on the Z!!!!
HOW COULD YOU COMPARE A FWD-BOXY TO A RWD-SEXY?????
But if you prefer torque-steer, of cos that's a different story!! LOL
Style wise it's really personal, when I look at a GTI, I'll say 'ok, a VW', when I look at my 370z, I'm like 'Yea.... sexy... I'm coming in now...!'
Also, don't you worry about reliability issue of VW?
Z only has one famous Screwing-Lock Failure, but for VW, my past experience is..... Screw-You-Anything-Failure.
Have fun test driving both and look forward to hear from you!!!