1. Why is it the protagonist is not allowed to spend the night for free in his own home? Try sleeping on the ground in Candlekeep. The silly guard tells you to go rent a room from Winthrop. Candlekeep must be in dire financial straits to force money from its own residents for room and board.
2. Why does the Friendly Arm Inn allow anyone to sleep within the compound? Sleep in any town and you'll be awakened and accused of vagrancy. I guess that's why they call it the FRIENDLY Arm Inn. Still, sleeping outside the keep would be better if they had a few park benches out there...
3. Why does Candlekeep forbid most guards from carrying swords and then sell all sorts of weaponry at the store? My guess is that it's more profitable to keep swords away from guards and sell them as souvenir's to the tourists. Either that or they provide loans to the visitors. "Hey, look what I got at the library! They said I had to return it in two weeks, though."
4. Why do assassins believe crowded inns to be the best place to slay someone? Haven't they ever heard of using the cover of darkness, waylaying in alleys, or using subtle means of extermination? Apparently not. If the Iron Throne can afford to hire entire mercenary bands to prey upon merchants, why couldn't they get some competent killers, too? The answer is probably nepotism. I bet all those higher-ups hired their friends to do the job.
5. Why do hobgoblins have blond hair after you scalp them? Have you ever seen a live hobgoblin with blond hair? I didn't think so.
6. Why do stores buy bounty notices and other such documents? Do they want to ship them out to be used again? Is it a conspiracy to get the protagonist killed? Or is it part of a scrap paper drive to save Toril's environment? Personally, if they're going to do that, I'd rather have them make landfills on top of ancient druid groves.
There will be more to come later.