After 3 weeks of “pending approval” my landlord went to CW to file first time in person. A month later I still haven’t heard if she was successful with the online application.
Yes. There is no requirement that you live here. It is a multiple entry visa. You will be stamped in for 1 year each time you enter. Enter near the end of your first year and you will get another year.
Unless he can simultaneously meet the monthly income method and decides to use that instead when he applies for the next extension. You can choose either method at any time provided you can meet the yearly requirements when you apply.