What if I create a whole new chain? Will the transactions at the very beginning of that chain have to be added to the big, old chain? How far back do the common ancestors of two chains have to be for your auto-merging to happen? What happens if two histories conflict? Then in Version Control parlance, we have a "merge conflict".

What stops me from doing a hard fork to roll back both blocks?

You have two competing chains: Chain 1 and chain 2. On chain 1, you spend a token on a good. On chain 2, you spend no token. You wait for chain 1 to win the race. You then stake on chain 2 to get your money back. If chain 2 then overtakes chain 1, you've executed a double-spend attack.

An equivalent attack wouldn't work on a PoW chain. If you do the equivalent of "staking" on chain 2, then you're computing hashes, which is costing real-life resources. In the PoS case, without slashing, staking on chain 2 is free. In fact, this is the rational move to make every time you spend a token; stake on competing chains to get your token back.