I think you raise a lot of good points. A fun aside; the first episodes I clicked on were an early one from season 1, and a random show from season 2. During the season 1 show, my wife butted in with, "This is barely television!" (That means, if I ever watch one of the earliest-taped Double Dare shows with her, she's just going to rip the remote out of my hand and turn off the TV.) In the middle of the season 2 show, however, with Phil in full sing-along-with-the-music-mode, she gave Phil props for what he brought to the show, and how much more coherent it felt.
That's a long way of agreeing with what I've heard from a number of people going back to watch these, including members here: Nick Arcade was a fun idea and fun to watch, but suffering in execution.
Believe it or not, I was more frustrated with the Video Challenge as a kid than I am now. My observations in first run -- in no particular order, and surely influenced by the episodes I had seen: I've never heard of these games. Why do they always wager more points than they have? Why don't they know how to play this?
The first complaint can't be remedied, because they made whatever deals they could for real games. But the rest could have been fixed if they had more time to work with the kids. A Video Challenge at its worst felt like me renting a game from Blockbuster that didn't come with a manual. So I'm left to wonder: did the kids not play them at all? Or did they only get their hands on them for a short time?
Years later, I can't help comparing this portion with Starcade. Arcade games probably lent themselves better to brief timed challenges over many of the titles on Nick. At the time, my brother and I were rapidly building our SNES library, while our friends down the street had a Genesis. I felt smack dab in the target group for the show, and yet, I wasn't bowled over by a Video Challenge. There was something missing to bridge the gap (for viewers and contestants) when the game was unfamiliar, or fairly complex for a 30-second session.
Also, I was, and still am, a fan of Get the Picture, so the video puzzles were welcome events. But I agree the Pop Quiz was not working, particularly in season 1.
I feel the same lack of practice goes for the Video Zone too. It was rewarding to see a kid trying to dodge the obstacles, even if they didn't succeed. It was the opposite of fun when a kid walked across an entire level like it was a still painting and got hit by all 9 enemies in his path. Given how many variants on Pong we saw in the face-offs, I imagine they were in an overall crunch of time and budget, but I feel like there was a way to make it better by adjusting the power bars, amount of enemies on screen, speed of the game, etc.
-Jason