Canadian buying in the US

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October 03, 2023

by a searcher from Ivey Business School at Western University in Calgary, AB, Canada

Anyone have tips of what needs to be considered as a Canadian looking at a deal in the US? Challenges and solutions both welcome. Thanks!

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Reply by a searcher
from IE Business School in Florida, USA
Agree with both commenters above. The corporate and tax counsel you choose will be essential to your peace of mind… during, at and after closing.

Canada Revenue Agency (CRA) reporting requirements on US investments is cumbersome (and defy logic in many occasions). Make sure you engage a CPA in Canada that is versed in US investments. Get a capped fee agreement for tax compliance (hopefully capped at CPI for future years) as the Canadian requirements are a lot and increase in complexity every year that passes.

Also, consider that the CRA does not care about US tax due dates. While you may file an extension in the US, you may not have that benefit available in Canada. So, it is basically a risk to let your US tax return linger. Better to be proactive and file both earlier in the year.

Specifically regarding structure: discuss with counsel the ability to put a C-blocker structure that complies with the US-CA tax treaty to ensure you don’t pay more taxes that you have to… or at least take advantage of a potential deferral mechanism.

Also consider the immigration laws, as US and CA customs will question your multiple entries to either jurisdiction if you don’t have a working visa.

Have done both: investments in Canada with US investors, and investments in the US with Canadian investors.
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Reply by a searcher
from University of Manitoba in Vancouver, BC, Canada
Buying - A Canadian (either as an individual or corp.) can buy as USA business (either directly or through a USA holding company). Tax implications are real. There are for example massive penalties for not filing certain USA tax reports even if you have zero activity. You'll also need to declare all your USA/foreign income on your Canadian taxes.
Working - If part of your plan is to live & work in the USA, buying a business can be a great way to make it happen. Yes there are E-2 Visas and other tools available. If the business is of sufficient size, it can go through the sponsorship process to get the new owner whatever it needs.
As others have said, it's doable, just get good cross-border tax advice before you do anything. If it's a material size, there are all kinds of off-shore structures to minimize taxes, but they're complicated to setup and maintain.
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