The only reason I can think of for somebody wanting to use a legacy address would be for message signing. There is no benefit to using this type of address.
Message signing is the complain some people do make, but it is not just a genuine excuse because I signed my first message using segwit (bc1q) address when I was a newbie.
There isn't an official standard when it comes to signing messages with segwit addresses. If you did sign a message it might not be recognized as valid when you try to verify it with a different wallet or program.