Chris, in the UK, if the punctuation is not related to the quote it goes outside the quotation marks, such as commas and periods (full stops). In your example, you’d leave the question mark inside the quotes, because the the question mark is part of the quote.

For the second part, once we learn the rules of punctuation we can choose which rules we’d like to break to enhance our writing style. It’s always good to be thought-provoking as long as you’re intentions are good. This is all personal opinion and specific to the writer.