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Depends on if IFR or VFR, and destination. IFR always, VFR, if desired.
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Too complex to cover them all but there are exceptions.
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Generally yes but you'd need a PilotAnon for the latest.
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Not really. Some do some don't. Depends on the airport.
Bottom three:
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yes, both
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Eventually, sooner if ordered
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Just pilot voice exchanges and airborne tracks