Entering US via car/land border on 90 day ESTA, exiting after 90 days via air/plane, re-entering via land to begin another 90 days

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The simple fact is, you're very likely to have problems.

What you are describing is very clearly a "Visa Run", and even if it's technically within the rules of what is allowed under the VWP (and whether it is or not will depend on the exact details, many of which you haven't provided), there is a very real chance that you will NOT be allowed re-enter the US on your second attempt if the immigration official decides that you are doing a Visa Run.

Instead you should likely apply for a US B-2 visa which will allow you to stay in the US for up to 6 months at a time.

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Entering US via car/land border on 90 day ESTA, exiting after 90 days via air/plane, re-entering via land to begin another 90 days

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