Serbinski Accounting Firms

You don;t report SS on a 1040NR, because you are Cdn resident. But the SSA form you got is all you will get.

That would be a call to Vanguard. Nothing has changed, but you will be withheld 30% unless your withdrawal is "periodic", which each broker has its own definition for.

Sounds right.
Btw, if your RSU payment was less than $10K US you can exclude it on your Cdn return, by treaty.

Not likely. They know the rules.

The date acquired.

There is a difference between non-taxable and not reportable. Your W-2 income is to be reported in US, and then exempted by the treaty article you mention.

You would report it on a 1040NR.

I assume you mean spousal RRSP.

You would report the entire amount (before tax) as pension income on 1040. The taxable portion would be the growth since you moved to US.

The 25% tax would be used on a form 1116 to write off against the US tax that you owe on the taxable portion.

1. Correct
2. No need to report.

You need receipts for any claim to adjust cost basis to be approved.

No. You MUST pay tax in Canada (and US) on the sale. You will get credit for the Cdn taxes on your US return.

not sure what an SRSP is. Clarify.

Leaving it until you stop working.

Yes. fund as much as possible, your Roth401(k) while working vs. your 401(k). Then when you stop working, but before reestablishing Cdn residency, convert as much of your 401(k) as you can, paying US-only tax on that conversion at that time, making the Roth portion non-taxable forever afterwards.

Then you can claim medical expenses on the NR return, but since you are not reporting world income, your deductions may be limited.

If it is not working with the software you are using, contact them.

No. You need to have foreign income that is taxable in US. In this case it would be best to take the 25K of tax as a deduction.