Re: Wk2 not upshifting on hill
I think it's normal. I noticed when I let off the throttle to coast up to RR crossings that the transmission doesn't go into a freewheeling type neutral like my older trucks. It slows down faster. I think it has something to do with the lock up torque converter operation. Once you get used to it will be second nature, it's just different.
I do have the two speed transfer case but it sounds the same as what you are experiencing.