Yes, the trade in might be a problem. We were looking for a replacement for our 1997 Triple E in 2008. The dealers in the US were not interested in a Canadian registered vehicle, though of course the Dutch Star would have been made in USA in the first place. The problems could be several-, most minor such as speed and mileages in miles, weights and load limits in kilograms and what may be the biggie, exported to Canada without the original post manufacture taxes paid.
I think your best bet would be to contact a US dealer about a suitable rig and see how much interest they would have in your trade in.
Where we bought out current Itasca Horizon in Mesa AZ, when we remarked on a 38' Triple E Commander the salesman perked right up and said "Right, you're Canadian! I can make you a huge deal on this, probably near wholesale. We'll probably have to wholesale it out to a Canadian dealer and there will be transport charges on top". Unfortunately it was too large for our driveway parking so we had to let it go. (Didn't ask the price) However we are still happy with the Horizon. Importing wasn't much of a big deal but you MUST follow ALL the steps. If it doesn't pass inspection it has to be out of the country in I think 45 days from date of import.
