I don't like helicoils for a lot of reasons. What you should do is repair the pan using a TIMESERT. Timeserts are solid, cylindrical inserts that "lock in" to the damaged threads and give you brand-new solid threaded hole. You can put your original drain plug right back in with no worries. The LAST thing you want is that drain plug to fall out while you are riding. As a shop owner, the LAST thing I want is that drain plug falling out . . . a very bad way to lose a customer! I have done this repair many times, and would be happy to do yours.
If you are wary of repairing the pan, replace it. Don't fool around with this! The repair either has to be done right, or the pan should be replaced. As GSXcite said, oiling down the rear tire is not fun, and is a good way to see your life pass before your eyes . . .