The old lady in the market could give him a lottery ticket to collect and he runs off with the cash.

As for the duel falls, I'd cut a few of the first falls (it's a little too repetitive) but once the idea of jumping up again kicks in you could have him just miss (which works perfectly) then massively over jump so he goes right up in the air out of shot and then comes down again and then have Bobs shot of him looping around the bridge (the comedic rule of threes is usually a good guide).