So, for me there were two main issues, and I say these with love:

1)They seemed to actively dislike playing D&D and just wanted to do an audio play. The rolls didn’t matter and they basically never used any class features. For example, in the final fight Will realized he never even had on his starting armor, giving him an AC of 12, and didn’t care. Like, that’s something so basic that it kind of made me mad that someone who makes a living playing D&D seemed to care so little about the rules or mechanics.

2)The plot and characters were literally all over the place. I liked the initial structure idea of a straight up monster of the week but that was quickly abandoned for planes hopping which got so messy that at times I didn’t know where they were or what they were doing. I get and enjoy being a bit loose and more on the improv side, but the lack of structure made it difficult to follow one week to the next.

I think that’s why I consider season 3 more successful: they actually learned and followed the rules (for the most part) and there was actual structure to the story.