i) I do not know a great way to do, but I'll try to make a proof. He will eventually get to $0$ or $500$ since he moves up one dollar or down one dollar without a pattern that restricts the $0$ or $500$ option.
ii) The probability is $\boxed{\frac25}.$ The only thing I can think of is states. First, try $0$ or $400$ and they go to either one with probability $\frac12.$ Then when at $400,$ it can go to $300$ or $500$ with equal probability too. At $300,$ it can go to $100$ or $500.$ At $100,$ it can go to $0$ or $200.$ This has five variables and is much simpler to solve. Specifically, find $b$ in the system of equations $b=0.5d,d=0.5+0.5c,c=0.5a+0.5,a=0.5b.$ Solving this gives us $b=\frac25.$
To clarify, in each multiple on $100,$ we try either a) The amount of money needed to reach $500$, if possible, or b) If a isn't possible, then double or nothing. Since it has equal probability in each step, the states in the better idea are possible.