I've had to have my sump helicolied but oil still dripped out a bit, even after using new plug and washer, so I put some copper silicone seal on the threads near the nut head. It does not leak now, and leaves minimal trace that I can see when removed - hopefully if any does peel off it will end up in oil filter.
Use loctite - 542 is fine.
Actually re-reading this, don't use loctite or silicone for that matter - you run the risk of pulling the helicoil out with the sump plug - see if you can find a hard plastic gasket washer that will fit the sump plug and use that. Next time you open the sump plug ensure that the gearbox mating faces are clean and not damaged, same with the sump plug.
If the plastic washer doesn't work in (I think it will) then just before you nip the sump plug up put 5 turns of natural gas grade PTFE around the threads so that it will form a washer of sorts when the plug id tightened.