sitting at a table in a physical DND game and rolling a 2 on an insight check with your character's 18 wisdom is no different than failing it in the game. is it frustrating? yeah. but that's what the save scumming is for. it's tedious but if you aren't content with the outcome your rolls get you, you reload and do them over and over again until you get what you want.
as far as game difficulty goes, I've found that combat difficulty was the worst for me when I was playing a fighter, with the cleric, rogue and wizard in my party. but now I'm running with 2 warlocks, the cleric and a fighter and honestly? warlocks wreck face really fast. Hex + Eldritch Blast is no joke, I've done 20 points of damage in one go.
