Okay -- in your opinion, where's the best place to stop to file the ADIZ
plan?

There's no need to stop anywhere. File the plan from home. Pick an
entry point outside the ADIZ (the briefer will give you choices -
typically a VOR or intersection) and an entry time.

Be there within (I think) fifteen minutes of that time (or update your
flight plan in the air).

Be high enough for radio reception and radar coverage (no problem for
you Jay!), and be sure NOT to enter until you've gotten your sqawk.

Jose
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