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Exactly. If they plan to use of an Umbrella company, it really makes sense to use one that can handle cross-border matters and is located in Canada. In any event, the Umbrella company should be struggling with these questions and matters, not you. They're providing a service, and it's not free.
 
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Exactly. If they plan to use of an Umbrella company, it really makes sense to use one that can handle cross-border matters and is located in Canada. In any event, the Umbrella company should be struggling with these questions and matters, not you. They're providing a service, and it's not free.
Found this thread that might provide some insights. I didn't read through all of it, but looks like most individuals in a situation similar to yourself chose to go the freelancer route.

https://britishexpats.com/forum/canada-56/working-remotely-uk-company-while-ontario-915476/
 
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Thanks mate, much appreciated.

Just one thing, is it definitely a requirement that estimated income has to be reported to CRA on a quarterly basis? Can't I just do the annual tax return?
 
I'm not sure. My best guess based on the tax lawyer's recommendation in OP's post is that CRA expects regular (quarterly?) tax payments. Perhaps you'd be charged an interest penalty if you just pay at the end of the year. I don't know though.