Q: Does the word "stretch" mean the same thing in "Running at full stretch." and "By no stretch of the imagination."?

A: the same meaning

Q: Does the word "flip" mean the same thing in "You need to flip the pancake onto the other side." and "Flip over the pork chop."?

A: the same meaning

Q: Does the word "lot" mean the same thing in "A lot of money." and "He bought a lot on the lake."?

A: different meanings

Q: Does the word "confidence" mean the same thing in "After that failure he lost his confidence." and "Everyone trusted him with their confidences."?

A:
different meanings