You can do it with an ESTA, as long as you don't spend more than three months at a time in the US. Crossing into Canada/Mexico (or flying home) 'resets' it. I don't think there's any rules on how long you have to leave for.
Getting the vehicle in is completely separate to your visa.
You need (in theory) to have approval in advance for temporary import of a foreign vehicle. Search 'EPA Exemption Letter' on here. It's easy enough to apply for, and you can do it all by email. I say in theory because they never asked to see mine at Newark Airport, and I imagine they're even more lax at land borders - but there have been stories on here of bikes getting stuck in customs for a month when they asked for it and the owner didn't have it.
There's a three month limit on that as well, but again I don't know how accurately it would get recorded at the land borders. Might be worth planning to leave the bike in Canada.
Oh and the one time I got pulled over (in North Carolina), the cop was certainly aware of the import exemption - I passed him vehicle reg, drivers licence, etc one by one, and when I gave him the exemption letter he said "that's what I was looking for".
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