Well, maybe Gandalf had a plan to enter Mordor through a secret passage like you propose, but I find it severely unlikely that Gandalf had no plan, perhaps no final decision, buut still formulated plans. The fact is, however, that we do not know because Gandalf did fall and did not lead the company into Mordor, nor was he meant to so this speculation would truly change the entire trilogy, perhaps the eye would have seen them if Gandalf was with them as he has immense power and Sauron could sense power, as evidenced when Frodo claimed the ring. Maybe the main reason that the hobbits were able to make it all the way is the comparatively small amount of powerpresent in them.
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