When you play with a set group, much of the ‘content’ is experiencing the stuff together, so even bugs or grind can become a source of amusement because you have 10 people in vent bitching about it and laughing rather than just you smashing your head into it solo.
This is something I address frequently, but from another direction. If you the player are supplying most of the ‘content,’ it does not matter what the game is. We just need something as an excuse to do it together. I, as the customer, tend to demand that the game keep up its end of this transaction by contributing something, sometimes anything to the process. It is dumb to pay a monthly fee to a company that is not comparing favorably with playing Hearts. Many games contribute negatively, making it harder to play with your friends. Don’t pay for that.
Just because you had a good time does not mean that it was good. “So bad it’s good” is still bad. The items SynCaine cites are still bugs and bad grind, even if you can find a way to enjoy them. It would be objectively better to have good content to share and discuss, rather than simply “misery loves company.”
Our guild has a lovely time gathering for the 30-second cut scene reveal, but the event did not add much beyond creating a Schelling point. We created the content by being there, but we can/have done that nightly be declaring guild events. We had a guild event the night before: the Mad King’s Clock Tower. Many of us had a good time talking, groaning, sharing advice, shouting about norn and charr, adjusting graphics settings, etc. We all got the achievement. We appreciated the art, and we recognized which aspects were not conducive to a good experience.