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Thinking of retiring to Canada – Tax and Investment Questions


Hi Phil

I found your contact info through the facebook group for Americans in Canada. Great group by the way, we’ve learned a lot for far.

My wife and I (she’s Canadian and I’m American) will be moving to Canada in late 2021 and we have some planning questions that will need to be answered before then.

Here is a quick breakdown of our situation:

  • Moving to Canada in late 2021
  • We will be selling our house in California before we move and are hoping to buy a house in Victoria soon.

IRS Guidance on Second Stimulus Payments

The US treasury and the IRS have recently released some guidance on the second stimulus payment. I’ll outline a summary of these updates below:


The IRS and the Treasury Department expects the first American taxpayers to receive their payments starting this week.

Taxpayers are not required to request payments as stimulus payments will be made automatically to those eligible. Eligible taxpayers that filed a 2019 US income tax return or those that registered for the first stimulus payment will be automatically be sent payment.… Read more...

18 Year Old Working at Starbucks Owes $8,000,000 in tax??

I would normally not point out someone else’s mistakes or omissions. We all make mistakes and should only be judged based on how we take responsibility for these errors and subsequently help to resolve them.

Being a public institution, however, we should hold the Canada Revenue Agency to a much higher standard. (note that this assessment was released a few years ago as I didn’t want to post anything until the case was fully resolved and had permission from my client).… Read more...

Update: Details of Second Stimulus Package Announced


With the second stimulus package expected to be passed by Senate on Monday, December 21, and passed into law soon after that by President Trump, the details are becoming clearer on the payment levels Americans can expect:

Stimulus payments: The new package includes $600 stimulus checks per adult and child. The amount per adult is half of what was provided under the original CARES Act in March. The amount per child is slightly larger than CARES provided. The new bill will also allow U.S.… Read more...

Update: Agreement on Second Stimulus Package Announced


Sunday, December 21, and a deal has finally been reached on a second stimulus package. After months of partisan stalemate, the 4 leaders of the Senate and Congress finalized an agreement on a package that will include $600 stimulus checks mailed to millions of Americans within a few weeks. Moments after the deal was announced, Senate Minority Leader Chuck Schumer predicted that “barring a major mishap,” both the House and Senate could vote as early as Sunday night.

Leaders reached the agreement after days of around-the-clock talks and as they felt increasing pressure from colleagues and constituents to pass to at least some coronaviruses help before the end of the year.… Read more...

ROTH IRA and TSFA Questions



This is Erin from the recent question about what to do with American investments.

A little about me:

I make 12k USD per year through remote work for an American company.

I make about 30k Canadian self employed income.

Is it possible to invest in both TFSA and Roth IRA? Should I not bother with the IRA and just invest more in Canadian accounts?

I just recently changed my Chase Bank address to my Canadian address (I just forgot to do it until now), and it basically froze my investment account.… Read more...

Citizenship Based Taxation is not going Away, but these 5 Changes Would Change the Game (for the better)

Many Americans living abroad have been advocating aggressively for the repeal of Citizenship based taxation (CBT). These advocates argue that the rules that tax US citizens abroad are unfair and overly punitive.

Although I do not entirely disagree with the arguments against CBT, the current US tax expat structure would have the be overhauled if citizenship-based taxation was abolished. The US would have to implement a more comprehensive non-resident and exit tax system to go along with these potential changes.… Read more...

The CRA, Cryptocurrency, and Voluntary Disclosure


On September 18, 2020, the CRA applied to Federal Court in an attempt to obtain client’s confidential tax information from Coinsquare Ltd., a Toronto-based cryptocurrency trading platform. Included in the application was a request to view trading and holding information. This filing is one of a series of significant moves by the CRA following its promise to put new emphasis on enforcement focused on several digital trends, including the rise in prominence of such cryptocurrencies as Bitcoin, Ethereum, XRP, and Tether.Read more...

Update: Corporate America joins in call for second stimulus package deal


With the progress of the so-called compromise package bogging down in recent days, there is growing concern that a second stimulus package will even get a vote on the Senate floor before the holiday hiatus. A key focus of the current stalemate is a debate over whether the Act will include details for the distribution of individual stimulus checks and if they are included, the exact amount of the payments.

Most Democrats and a progressive coalition that includes Bernie Sanders is pushing for individual checks to remain at the same level established in the initial CARES Act ($1,200 per adult and $500 per child) while most Republicans, including President Trump, are pushing for $600 individual payments.… Read more...

Update: Second Stimulus Package Compromise Proposal Gains/Loses Traction


Thursday, December 3, opened with a report that outgoing President Trump acknowledging that he would sign a coronavirus relief package if Congress can broker a deal in the coming weeks after months of partisan-driven deadlock. “I want it to happen, and I believe they’re getting very close to a deal,” Trump said, having previously urged Congress to “go big” on coronavirus relief. But he does not appear to be playing an active role in negotiations or in the broader pandemic response as his time in the White House ticks down.… Read more...

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