TurboTax U.S. tax experts are knowledgable about international tax from a U.S. perspective. You will need a TurboTax Live product (Basic, Premier or Self-Employed) to get year-round support from a credentialed tax expert such as an Enrolled Agent, CPA or Tax Attorney. They may or may not be able to advice you on cross-border situations.
TurboTax Canada offers similar services. You may wish to contract them about your rollover questions.
Depending on your situation you may have to file U.S. and Canadian income tax returns. U.S. citizens and resident aliens are taxed on worldwide income. However the IRS offers a foreign earned income exclusion and a foreign tax credit or deduction.
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