If one obtains a Reentry Permit before departing, it is unlikely he or she will be accused of abandonment with regards to U.S. residency. Having said that, it may still come up and strong proof of continuing ties and an intent to reside in the U.S. are important to have at the POE. Speak to an attorney about the particulars in your situation for advice.
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Where his two re-entry permits approved? Did he use them?
These dates look bad ... he should talk to a lawyer about getting a SR-1 visa at the US consul.
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Seems that he has gotten his re-entry permit. A lot of absences though. he should have documents to prove everything you have described. However, no one can tell you exactly what will happen at the border. Will depend on a particular CBP officer.
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Not necessarily, even though this looks pretty bad, contact an immigration lawyer immediately.
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