Great review and great history lesson. I remember Video Days, but I totally forgot about Questionable. I always like The Reason and Modus Operandi. Anything with Marc Johnson or Mark Gonzales.
With skate., I never actually finished the game, instead opting to roll around the city endlessly while tricking off of whatever caught my eye. While I like the expanded trick repertoire and the ability to get off my board, I do miss the greater degree of character customization and the ability to choose a style for my skater. It may have seemed subtle, but to me, having several style options made sure that not everyone skated exactly the same. Being able to make yourself in the game and give your avatar a similar style was important to my enjoyment of skate. I also feel like the new look of skate 2 uses too smooth a framerate and too few camera effects, which is somehow distracting. I can't quite explain it, but sometimes aesthetics matter.