I think we can all agree that choosing one painful death over one painless one would be wrong (okay, except for Zamboni_Driver), and that's true as you extend to some degree upwards, but any amount of extra deaths looks really bad as a serious answer. Which is probably why you're getting mostly jokes.

I think a painless death and any non-100% chance of a another painless death would be preferable, so I'll say sure to the limit point of 2 deaths. If it was me and I could die more than once, I do it a lot to avoid the excruciating pain, but then again that doesn't really make sense. If it gets to the point where I'm talking about genocide amounts of deaths I guess I'd have to torture the one poor soul.