You need to roll a 1 out of 20 to have a chance to level up??? That is really dumb... Overall what did you think?

It's a symptom of the game's basic design. Given that encounters and enemies are for the most part random, leveling has to be a little more restricted in terms of its frequency and cost.

By making leveling random (and rare) it means players aren't going to bankrupt the experience pool and constantly haggle over who deserves to use the shared resources more. So players won't be concerned so much with leveling their character as finishing the quest on hand.

I have seen a lot of negative comments on the 20 to level up. I personally consider it a substitude for the awesomeness of rolling a 20, which was a crit in the old days and at least an automatic hit later on.
They needed something that adds the feeling of getting lucky rolling a 20, and since leveling up is not absolutely needed, I think its a cool way to add some fun bonus to rolling a lucky 20.

Well done! This looks like it takes the best from the bogged-down Descent and the too-luck-dependent Dungeonquest. Have some GG.