Re: 22 Black Powder ammo?
Crimping the case onto heeled bullets is typically done with a wire stripper, whose sharp-edged hole is dulled with a rattailed file.
I do this when I reload .32 Long Colt ammo with heeled bullets.
An inverted .17 Remington case could be used to flair the case mouth slightly, after removing the bullet. Add the black powder. Seat the bullet and crimp it into place with the wire stripper.
Remember, the priming compound is in the rim of the cartridge, so carefully cushion the case's base while seating the bullet.
It could be dangerous to make your own black powder .22 cartridges, since you're using black powder in a rimfire cartridge. Whether you wish to pursue this is entirely up to you. I'm just noting how it could be done; I make no claims to its safety.
I load black powder in center fire cartridges, but have never tried it in rimfire cartridges.
The decision to do so is entirely yours.
"Therein do I see an ugly cat. Smoke. Fire. Brimstone. A vast desert. Holes in parchment. The ugly cat is much amused." --- The quantrains of Gatodamus (1503-1566)