There's a trick to making the game marathon-safe in permadeath mode. If you die in permadeath mode, just ALT+F4 to quit the game immediately on the death screen. As long as you don't hit the Quit button on the death screen, you will still have that save slot intact at the last point where you saved. There is one caveat to using this hidden feature: it automatically saves your game time. So if you die in permadeath, you are guaranteed to have a longer play time but at least you can recover the save and continue the run. This trick is also very helpful for learning routes in permadeath mode.

Alternative: Tie the Victory Emblem to going Swordless. Once you have it, remove the normal barriers that would require a sword. That way Newbies would have to take the sword on a first run, but once you clear the game, you're assumed to know enough about it that you can attempt it without the sword. And just have Permadeath mode negate the Emblem requirement.