I have done this many times, and a few times it has even been my fault :redface: ('83 Nissan pickup and a mid-sixties Johnson 40hp.)
You can do this with the head on. I like the threaded sleeves instead of the helicoil, but have used both without problems. Take a really soft knit and toothy cotton rag and cut a long strip about 4 or 5 inches wide. Poke it into the spark plug hole you are going to rethread with a screw driver. Don't push it in deep- leave it touching the head. Tap the hole, vacuum it out, snake the rag out with a bent wire to bring out all the metal shavings, run in the insert according to package directions. I have never had a problem with metal filings using the soft cotton rag method.
Note that spark plug torque is usually fairly low- sometimes just a few foot pounds. And spark plugs in an aluminum head don't come out as well when the head is hot. Always start your plugs and run them well in by hand, not ratchet. After the metal gasket seats by finger tight, then you can torque it properly.
(If you feel you have to remove the head, you need a manual so you have the right torque specs.)
Done.