The elven frailty is wine. The elvenking's butler and the chief guard drink some wine, which caused them to fall asleep. This gave Bilbo the chance of stealing the keys to the jail cells, and escaping with the rest of the dwarves.
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Bilbo's escape plan is mediocre. He risked the lives of the dwarves while trying to carry it out.
The dwarves were captured and imprisoned by the elves in Mirkwood. Bilbo had to keep entering to form a plan and carry it out.
It was mostly gold and jewlery.. THey loved that stuff
Bilbo found the hidden exit in the palace of Elvenking. He makes a plan to make dwarves out of the palace. He put all the dwarves into the barrels with many plants that can protect them, and rolled them out of the secret exit. And under there, there is a cold lake, which will lead the hobbit and dwarves to the Lake Town
Use Situational Awareness to think about, prepare, and plan for escape.