I just accidentally deleted a long, over-wordy response. This time I'll be brief.
First, you can fly into the US from either Canada or Mexico, subject to political considerations and negative COVID test. You can truck your bike across the border from either Canada or Mexico. This eliminates your "no go for the whole trip."
Second, if you're so short on time, why are you even considering riding from wherever you are in Canada all the way through the US? That doesn't make sense. If you've got enough time to do that, you can opt to take things far more slowly in Mexico and Central America.
Third, whether short on time or not, surely you've noticed that January is not a friendly season for long motorcycle rides in most of the US and all but a tiny sliver of Canada. It can be done, but it sure helps to have an appetite for self-abuse.
Fourth, you might consider leaving your bike behind in C.R. or elsewhere, flying home, then coming back to pick it up at a later date.
Hope that's helpful.
Mark
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