Does Huffman coding always produce shorter codes than the Shannon code?
This is actually problem 5.12 in Cover and Thomas's information theory textbook; show that the probability distribution ${1/12,1/4,1/3,1/3}$ gives a counterexample.

And if you want a really nice counterexample, consider the many non-isomorphic Huffman trees you can make when you have probabilities proportional to $$1,1,1,2,3,5,8,13,21,34$$ (the Fibonacci series with an extra 1). Figure out what the maximum and minimum depths are for a Huffman tree with this probability distribution. This calculation will lead to a counterexample for your follow-up question.