Have no idea how he got to Savannah before the train, I'm assuming he went ahead to find Clementine's parents to use against Lee and Clementine or he was just lucky and got there before the train considering how many stops it did, and how long it got working. And for the walkers in front of the hotel thing, it's likely the place was clear when he first arrived, and when Lee's group first arrived (when he appeared in front of the house when Lee was burying the boy), since the walkers in front of the Marsh House were from the herd who came into the city at the end of Episode 4, and by this time he was probably already set up in his hotel room with Clementine locked away, waiting for Lee to come.
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