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I'm no expert, but this is what I've heard:
If everything about the aircraft and its documents is perfect and the aircraft has flown for at least 100 hours (the minimum), then I think importing an aircraft to Canada is not a big deal, but when it's imported it has to be inspected as if it's a newly built aircraft and if anything isn't documented 100% properly then it can cause very expensive problems. On the Flying BC podcast they interviewed an aircraft broker about this topic and he said to budget around $10,000 to import a certified aircraft. On that same podcast the broker recommended you find a Canadian mechanic who is familiar with the import process and fly him down to the States do the pre-buy. Because of the cost, it really only makes sense to import a fairly high value aircraft, and only when the CAD/USD exchange rate is favourable.
A few "gotchas" I remember from the podcast:
There's no such thing as field approvals in Canada, so if there are any of those in the technical log then that can cause problems. What counts as an engine overhaul in the US is not exactly the same as an engine overhaul in Canada, so if the "overhaul" doesn't meet the more restrictive Canadian standards then that causes problems. Any errors or omissions in a logbook or a lost logbook will cause problems. For an experimental/amateur-built aircraft, a pre-covering inspection is required in Canada but not in the US, so if an American builder didn't photograph every little thing before closing it up, then a Canadian inspector could require the aircraft to be opened up so every weld, rivet, bolt, and wire can be examined. That would obviously be very expensive and time-consuming, and it might be stuck at the border until it's done.
There are horror stories of people having to spend many tens of thousands of dollars to import a perfectly functional aircraft just because the builder or owner didn't document things well or because the buyer didn't know about certain red flags that could have been noticed during a pre-buy. American mechanics will not know about these Canada-specific things, hence the recommendation to fly down a Canadian mechanic who is familiar with the import process.
I think it's much easier to export an aircraft to the US from Canada because Canada has the more restrictive requirements.
I appreciate the very informative reply