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Very interesting, although I never seem to have luck with being granted permissions for things. An NPC will offer me a bed for the night because I'm strapped on cash and can't afford the inn, or buy the shack by the river, and they visibly say I can sleep there, but then the game will be like "can't sleep here." I try all the beds, but never have success. It's also kinda spotty on giving the player items after dialogue in where you're meant to be granted a key and such.

Am I doing something wrong?

In my experience it's a 50/50 change they'll give you access to sleep the night. It'll pop up over their head saying "Offers for you to sleep the night". My recommendation is to ask at least a couple times or spread the idea out between two messages or something. I find it 's more likely the game will recognize that you're allowed to sleep there if you warm them up to it first. Generally the spottiness of getting items from NPCs is a bit of a problem, but can be made a little more likely if you really "play things up" with NPCs. I have definitely noticed it's far harder to get items from NPCs in these more recent versions, unfortunately that's all the advice I can give.

Harder to get custom items anyway. Hang out for a game of Hazard at the tavern and Gareth will serve you a full buffet.

I've gotten things to work with OOC notes but even then I have to save scum, so it may just be a placebo.

It's good to know it's not just me being dumb. I imagine it's not an easy task to make AI work seamlessly with game mechanics.

It's been more difficult because I did indeed change something about the way this is checked. I might revert the change, since people seem to prefer actions sometimes happening inappropriately over actions sometimes not happening when appropriate.