You mean a sort of Pathfinder/dnd?

If I’m not mistaken, if you behave badly in life you are sent to one of the evil/chaotic planes; otherwise to the good ones. If you die there you die tho, no more reincarnation. And if you go to one of the bad planes, you will “die” in a way as to survive cause unless you are very special you are doomed to be eaten (literally).

Dunno how the actual religions behave on the matter.

Personally, while I hope that reincarnation is a thing it is mostly to not be afraid to die… after all, even if it were a thing I wouldn’t remember a thing about this life no? If I did, I would know right now that actual reincarnation is a thing. Since I can’t possibly know that reincarnation is a thing, and I don’t know cause I don’t remember a previous life that means it either exists but I don’t remember a thing or it doesn’t exist and when I die light’s out it’s over. In any case, for the living me it leads to the same problem(s).

Going back to your original question: assuming that we indeed reincarnate, with or without memories, then yes given an infinite amount of lives we will experience both the worst and the best