It's a game that's meant to be played multiple times, since you can't experience everything in one playthrough. I agree it can be frustrating when something gets locked out as easily as a failed roll, and that often causes choice paralysis in myself while I play, but you need to go in with the mindset of not being able to complete everything the first attempt (or you'll go insane).

I hope you can try the game again in the future and enjoy it! Maybe having several plays going at once and save scumming at choice points so you can use the same character for most of the options!