I completely agree with you on using things you find to adjust the rating. It would be super helpful and give a purpose for reading books and such. Honestly, I've been passing them over since I realized they serve no purpose beyond providing world-building and lore which, let's face it, ain't nobody got time for that if they aren't already knowledgeable about Forgotten Realms. I do actually have some good news, though. After some more playing, I did save the little girl. It took going in with Wyll's boosted persuasion from leveling up with guidance to knock it all the way down to an 11. Still barely scraped by with a 12 but I managed. So, I'd say the skill checks aren't impossible but you really have to think it through with who is going to initiate the conversation and what buffs need to be put on in advance and this is part of the problem. If you're going into a conversation with a new NPC and you have your entire party at your back, switching to another character should allow them to do that persuasion/intimidation/etc. roll.