Really interesting to read drisser, very well written and interesting that the most expensive car came bottom of the list for your needs!
I'm also considering changing my GTI for something more family friendly (mine's only a 3-door) and can't decide what to go for. We've got a nipper on the way in September and I could do with something a bit bigger... Possibly an S3 Sportback, maybe a 330d M-Sport Touring or I really really like the look of a Passat R-Line B-Turbo Estate with a few toys.
Looking at some numbers later in the week and will be talking to dealers about possible p/x. That said, I really love my GTI and don't really want to let go of it but had a trial run with baby seats and pram in the boot and with the new Isofix bases, the seat struggles to fit in between the back of the passenger seat and the B-Pillar... Hmm.
Sorry for sidetracking... Looking forward to hearing how you move forward!