[Sardy]

Let's assume, just for a moment, that at some point in time Hobbit lads and/or lasses did indeed stow away on a ship bound for Valinor, and that Gandalf was somehow directly or indirectly (or even accidentally) responsible...

Pure speculation, but what might the circumstances have been? The results of such an adventure (and "offense" to the elves)? And perhaps most interestingly, what might Gandalf's motivations for such spectacle have been? (We certainly know that the Grey Wanderer is prone to unusual, even seemingly preposterous, actions, usually due to faith or great farsightedness...)