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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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.