Let's assume the mempool is low when you do the transaction for the puzzle. If I send the coins with a fee of .1BTC and someone else finds the private key 30 seconds later and sends the transaction with a 1BTC fee, would they both be in the same block and the first transaction would win because it has an earlier timestamp, or would that not matter?
It doesn't matter, all depends if miners update the block that they are actually mining.