I agree that seasons 1 and 2 were harder, but I feel Tales was much easier. With Season 3 I never got stuck, but y first idea wasn't always right. With Tales my first idea would be right pretty much all the time, and often the annoying part would be getting Guybrush to let me do what I knew I had to do but that he hadn't figured out yet for some reason, or going through a complicated series of events or walking a LOT to solve a puzzle, making it more about walking around than thinking.
Honestly, Tales is probably the Telltale game I enjoyed least.
However, I think Season 3 is "easier" than Seasons 1 and 2 because it's more logical. 1&2 still had puzzles that made a bit less sense, while the Devil's Playhouse makes sense from start to finish. And it makes up for being "easy" (that is, not making you stuck constantly) by being longer. Definitely a more than decent size for the price. And its length isn't about making you move for ages to get to where you want, which is appreciated.
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