2) Yes the amount the program is looking for is all of your contributions since you opened the account for Roth IRA and Traditional IRA. If all of the money has been post tax money then it is not taxable when you take it out.
3) If the only distributions you have were rolling money from your IRA to a Roth IRA then they are not distributions received since you moved them from one retirement plan to another retirement plan.
Link to Massachusetts View of Non-Government Pensions
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