The problem with the 420 and 500 drain plugs is the case itself is super thin right there, and then there's that part that breaks off up above that supports the top of the drain plug, with a hole in the middle to let the oil drain out.
That's why, if you look at the Fumoto I used, I had to trim it down or it would have left quite a bit of old oil in the bottom of the motor.
Using a Helicoil will do the same thing, as the helicoil will stick up above the floor of the crankcase and not allow quite a bit of old oil to drain out.
That being said, I would not use a fumoto on a bike that sees anything but mud use (I could see a rock catching the fumoto, snapping it off, and bam, new engine) nor would I do it to a machine that I didn't intend to keep around forever. I did this on my wife's rig, she doesn't get too brave on it, we have NO rocks around here, only mud and water, and I made dang sure the skid plate was supported between the bottom of the motor and the skid so that the skid can't bend/ collapse up and rip the valve out.
On the other two 420's I've done, I bought used crankcase halves and replaced them, and I did the same on the extra 350 Rancher motor I went through recently. Of course, when you're tearing a motor down anyway replacing the crankcase half isn't a big deal because you're already tearing it down.
My father-in-law's 2006 Rubicon was stolen sometime this winter. He got it back a week or so ago, been ridden hard, put up wet. I suspect it may have been sunk based on the amount of debris I found and where I found it while cleaning it up, and more-so from the fact that the oil didn't look bad, but the drain plug was stripped out, and I was the last person to change the oil and I KNOW I didn't get torque happy when putting the plug back in.
Luckily on the Rubicons the case is thicker, so I'm going to tap it out oversized to a 14mm x 1.5 and use the factory drain plug from my Accord, which now has a Fumoto on it so the factory drain plug has just been sitting in the glove box. Will have the right 17mm head on it, just 2mm thicker on the shank.