Quoting TwoShadows "The breechplug MUST fit flush inside, while at the same time be turned so that the tang matches up with a flat on the outside of the barrel too."
I agree with TwoShadows and the others but actually there are three things which must happen at the same time.
First, as stated above the end of the plug must be tight against the shoulder where the bore stops and the rifleing starts.
Second, the flats on the barrel must be lined up with the top of the breech tang.
The third thing is the joint between the breech plug tang surface and the flat on the barrel where the two meet can't have a gap. If it does, it will look like the plug is not screwed in all of the way.
As I have said before, this job is a PITA. If you can pay a person a reasonable amount, AND he does a good job, it is worth the money. If he doesn't know what he is doing and just screws the breech in until the flats align and are tight without seating the breech on the rifleing shoulder then demand that he do it over.
As for price, Dick Greensides (Pecatonica River) charges $15. Money well spent!
As for drawfiling, if your pulling the file towards yourself, the file tang must be on the left side of the barrel. If your pushing it away from you, the file tang must be on the right side.
For a lot of information on files and filing, use the SEARCH button at the top of the screen and enter "Filing 101" for a write-up I did some months ago on the subject.