This one is the sort of thing where there are a bunch of assumption that shrouds reasonable on their own, but implasible in conjunction:
A1: you don't have to perfectly transfer your entire conectome to still be "the same person"; only things that are actually part of your current identity are needed
A2: if your identity changes gradually over time, even into something that if the change was faster it'd be considered disruptive, you're still "the same person".
A3: the human identity can be very extensively modified using behavioural techniques, hypnosis, and drugs that occur in the wild.
Then: you should be able to achieve immortality in a stone-age environment, by first modifying your own identity down to extremely small so it can be entirely transferred verbally, then modifying a victim more abruptly to a sufficiently similar state, and finally building that mind up again to be functional. Repeat for as long as you can maintain the dynasty.
EDIT: Hey! The OP specifically asked for outlandish ideas that seem like they wouldn't work! Am I just being judged relative the many ridiculously good posts here?
You know, I read a short story in which a person did exactly that: told his life story to a hypnotized subject, then convinced the subject that he had become the hypnotist. And apparently this had been going on for several "generations" now...
Thus spake Eliezer:
It seems that many here might have outlandish ideas for ways of improving our lives. For instance, a recent post advocated installing really bright lights as a way to boost alertness and productivity. We should not adopt such hacks into our dogma until we're pretty sure they work; however, one way of knowing whether a crazy idea works is to try implementing it, and you may have more ideas than you're planning to implement.
So: please post all such lifehack ideas! Even if you haven't tried them, even if they seem unlikely to work. Post them separately, unless some other way would be more appropriate. If you've tried some idea and it hasn't worked, it would be useful to post that too.