I saw the following on Bob the Oil Guy site and makes sense to me: "Most oil pan plugs don't use the thread for the seal ..they use the flat of the bolt head in conjunction (usually) with a washer/gasket. Sorta like a jar lid. The thread provides the preload on the sealing surface ..not the sealing surface itself." [sic]
If the threads are not maintaining the proper preload over time, you get the leak. To maintain the preload, you'll have to 'lock' the threads with a threadlocker - Loctite 243 and Permatex Threadlocker Blue are oil resistant AFTER they dry, which will take 24 hours to cure fully. But using a threadlocker on a bolt that needs to be removed periodically is not practical as you'll need to clean the threads each time you apply the threadlocker. This is where Blackness' idea for a Fumoto, I use the competing EZ Valve, should be considered. Once installed properly, you shouldn't have to remove it ever again.
I learned that Teflon tape is not a sealant, it's a lubricant that allows a threaded joint to be threaded tighter; it is the tighter threading that creates the seal, not the tape itself. If the oil plug has worn out threads, Teflon tape may not provide the proper seal. It could, but I think a threadlocker may be the better of the two in this case as it will 'lock' the threads in place, maintaining the preload on the bolt head necessary to prevent a leak.
Also, Teflon is not a thing; it is a brand, like Kleenex that makes tissue paper. I'm not trying to show off, it's something I learned tonight and thought to pass it on.