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As an extension of the "cofession" theory I've often though a big part of Gandalf's talk with Tom was to in a way get "permission" to leave ME, to have someone tell him it was okay to do so. Being clothed with the flesh of a man for so long would likely have led to Gandalf developing many of the mental quirks of being human and one of those quirks (at least for some) is a some doubt no matter how much one has actually done in service to others to qestion whether you have a right to ever stop, to say "I have done enough for the world, spent enough of myself in the service of others, I have earned the right to do this thing that I want." It's the bad side of being truly noble and unselfish (which Gandalf in his role in ME has clearly been) you feel a need to basically sacrifice yourself to the world , that being selfless means just that, having no self gratification at all, ever In that case what one often needs is someone outside of yourself who can give you permission to be selfish, to tell you its alright to be good to yourself, and that person has to be a person who you feel has the autority to do so. Given that at that point of "the talk" Gandalf is likely one of the, if not the, most powerful and higest level Maiar still "incarnate" and communcation with those in the blessed lands is impossible, Tom may be the only person who can fit that bill, the only spirit with the autority to give the absolution and permission that Gandalf needs to go to the West with a clean conscience.
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