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Also, try keeping the bobby pins in your stash box instead of in your backpack. You'll be able to still use them remotely for crafting when needed (in story mode, that is, not survival mode since for that one you need to have crafting ingredients on your person). Maybe that will prevent whatever bug's causing some of them to be lost.
For problem two, I think you have to knock out all of the guards first. If there's any of them alive from within the kidnapping compound, then the quest's not done yet. There's three of them, I think. After it's done, the chef should thank you and then offer you some chunky soup. You have to go right up to his cage's window.
After that, whenever you go back there, you should be able to get another chunky soup over and over (might be limited to one a day, though). The problem with it is that the soup usually disappears if you don't eat it right away. I've never heard of lock picks disappearing, but inventories in procedural games can do weird things sometimes. That soup always disappears, in my experience.
You're near enough to the beginning of the story, that starting over wouldn't be too bad, but you might not need to. If the lost inventory thing continues though (other than that reward soup which always disappears if you get it from the chef), then it might be a good idea to roll for a better random seed number on a new playthrough. That could get annoying to never be able to have a bobby pin or lockpick when you need one.