What I have done to thread up to a corner with a die is to tap the normal way as far as you can go, then flip the die around and go backwards. You can usually get another half turn or so. You still won't get right to the corner. Maybe you can reduce that area so that it doesn't collide with the mating thread?
If you are making a bunch of these, single point threading is going to take _forever_. I would recommend the die. Another option is to drill a hole and tap (making a knurled nut). Then locktite in a piece of all thread.
As to when to use what, dies are usually much faster, but if you really need your threads to be concentric with the shaft, you can't beat single point threading. I usually use a die if I can get a way with it.