Hi Ben - Rollin's advice is great for removing and cleaning up planking. It is amazing how much junk gets trapped underneath ribs and between planks.
If all you're interested in doing is re-tacking your canoe, I'd first ask why. Are the tacks rusted to the point of no holding power? Are you concerned about iron stains? If the tacks are no longer holding the planking on, you should re-tack. Pushing the tacks out from the inside isn't really an option because the tips of the tacks are clenched into the wood. They can't just be pushed out, and if you try, you might do a lot of visible damage to the ribs. If you're suggesting pushing the planks off from the inside it might work if the fasteners are really rusted away, but if not you'll surely damage the planking. With brass and copper tacks, you can get under the head with a tack puller (outside the planking) and roll the tack out. Iron isn't nearly as malleable as brass or copper so they will be more difficult to remove. Given all this, when I've re-tacked iron-fastened canoes, I've just placed brass tacks in positions next to the old iron ones, leaving the old ones in place where they were.
Unfortunately there may not be much you can do about iron stains because no matter what you do you'll be left with iron or iron oxide in the wood. If you strip the wood you can treat it with oxalic acid to remove iron stains but even with a great varnish job, they will return eventually. I believe I once read in WoodenBoat magazine about a technique for chemically altering iron oxide in wood so that it was "encapsulated" (the author's term, if I remember correctly), but since then I haven't been able to find the article again.