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I think you should be discussing these questions with your insurance agent, they are really insurance questions. Scott Smith, 800-743-1439, is very familiar with 337 insurance, if you need a good agent.
If you can make the insurance work, I think you can make the rest of your plan work. But remember it will take some hours to get an MEII starting from SEL CFII. You will need to be an instrument multi instructor to give the proper training to the owners for them to get a MEL Instrument.
Kevin
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