My tax accountant never gave me details about it, but I remember him clearly saying that there were serious tax consequences in doing so and that generally, thi

My tax accountant never gave me details about it, but I remember him clearly saying that there were serious tax consequences in doing so and that generally, this kind of setup should be avoided. If your structure looks like this: YOU-CA -> US -> CA (sandwich) and you sell your US company, the acquirer is stuck buying the CA as well, which is a pain for everybody. A US acquirer won't want to deal with a Canadian company. This is not the main reason not to do it, but it's something to consider.