If he was a juvenile he has not problem in applying for a new visa.
If he is an adult and did not comply with the terms of his visa he may have an issue if he applies for another visa. If he did not violate the terms of his visa and left before it expired he has no problem in applying for a new visa.
Kyndra Mulder's answer Based on the facts you have presented you are a USC and you should file an N-600. However before you take any action I suggest your read the N-400 N-400 all instructions and the guide to naturalization. Or consult with an experienced immigration attorney.
Kyndra Mulder's answer You must be suggesting ESTA because you will not get a visa in time for the holidays. You can only apply. ESTA may be denied if the service or BP suspect that you intend to remain in the USA rather than wait for your K vis through the consulate.
Kyndra Mulder's answer The scenario you have presented suggests you obtain an investor visa. This visa will allow you to come and go and live in the USA as yo prefer. However the visa is not necessary. There are many businesses owned by foreigners in the USA.
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