oskar, what I know and what I have done are sometimes two different things. I do know the Henry style of rifling was developed for paper patch bullets and that it really likes them. Too many articles and more than a few friends who shoot British doubles with Henry rifling surely cannot be wrong. However, I have never wrapped a bullet in my life. It is a step I just don't want to add, regardless of how historically accurate it is, which is more often than not a deciding factor for me...gotta be historically correct. While I don't like to revert to jacketed bullets, preferring cast, I will shoot jacketed to keep from patching bullets. The best I can do is refer you to The Cast Bullet Association and their web site. If it can be done with a cast bullet, someone over there has done it.
From what I've read about patching bullets your second suggestions sounds the best. I believe patched bullets are supposed to be dead soft and I am thinking that one patches to the bore diameter, allowing obturation to finish off the sizing.....but do not take my word for it! I may have to work up a paper patched load for one of my rifles just to learn about it.