I have had good success lately with asking Claude to do your last option. jj also works fantastically for this, because you can easily jj new up a bunch of empty changes with the descriptions you want to have, and then jj restore the state from your original stack into them. If the process goes poorly for any reason, you still have your original stack around.

You don’t have to do it this way, you could use the oplog to undo it all if it’s not to your satisfaction, but it’s much simpler than trying to edit the commits into the right shape directly.