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If I am asking a complex question, I would write it like this:
Do you have, by chance, three pennies on you?
Should I write a complex question that turns into a list without the comma?
Do you have, by chance:
- 3 pennies?
- 2 shillings?
or like this
Do you have, by chance,:
- 3 pennies?
- 2 shillings?
First of all, a complex question is something different from the sense I think you mean it here.
complex question A fallacy in which the answer to a given question presupposes a prior answer to a prior question.
Second, in a list following a parenthetical expression, you are entitled to precede the list with a comma.
Do you have, by chance, three pennies on you?
It is not necessary to add bullet points or use a colon or whatever. You can make lists with this, but they are not necessarily better than your first instinct.
You never need a comma and a colon back to back.
Do you have, by chance:
3 pennies?
2 shillings?
Seems like the way to go, to me.
Of the two, choose the first one: a colon without a comma. A list of items is a distinct construction with its own rules, so you don't need to replicate the structure of a conventional sentence.
Of course not, and the reason is simple:
When you start a list you use only the colon, and since you can't (except in other few cases) use two punctuation signs next to each other, the comma disappears.
