This discussion may contain spoilers!
To be honest, overall I thought Season 2 had better puzzles, better writing and fresher jokes than Season 3. I love TDP and think it's miles better than Season 1 (which I also love, don't get me wrong), but I think it's way more serious than Sam & Max should be. Season 2 was ridiculous, jokes were far more frequent and the puzzles were much more clever.
It's less that I'm comparing the entirety of Season 2 to Season 3. Honestly, I'm really most content with the last 2 episodes of Season 2 and think that those two episodes outshine Season 3 indefinitely. I really think Telltale had it perfect, or damn near close to it, with Chariots of the Dogs and What's New, Beezlebub. I actually think The Penal Zone is one of the best episodes of Season 3, easily surpassing 303 and 304. City That Dares Not Sleep was good, although I am a tad peeved at the ending (Max deserves a happier ending than that, honestly. I mean they're Sam & Max! They have an entire wing of Hell, LLC devoted to them! When did they suddenly start sucking at saving the world?).
The more I think about it, the more I decide that the problem with TDP is that they pulled way too many twists and turns and rose the HSQ too high. It's a remarkable game, but I think something just a bit more lighthearted story-wise fits Sam & Max better. I appreciate it, I just want to see something more light-hearted after that.
Anyway, do you guys prefer Season 2 (or at least it's last 2 episodes) to Season 3? If so, why?