#1, pick Claude Matthews as your running mate. Quite frankly I think that his values might have been entered in wrong, as he gives you a nice boost compared to the rest of the field.
#2, ignore the West (you'll win it if you're pulling ahead anyway), focus soley on the midwest.
#3, moderate on everything but labor issues (who already distrust Bryan so he needs to go hard for them to win them over).
#4, keep the south happy (no condemning lynching, be okay with being in bed with the former Confederates, etc)
That typically will ensure a large win. The trouble is getting New York on board. To get it, you need to:
#1, Choose to campaign heavily in New York
#2, pray that some the New York related events pop up. When the Tammany machine comes knocking, I just promise them no prohibition as the country doesn't like it if you fully cave. That will give you a little boost in the state. Another event is whether William Randolph Hearst will support you. He wants you to back imperialism (Bryan was historically anti-imperialist for his time). Doing so will give you another small boost in NY and CA.
It's fully a crap shoot whether or not you'll win the state though, much less pairing with the wide victory above.