Your penny scenario is flawed because you assume you will lose on the first trial. What if you win, or win 30 times in a row. By simply looking at only the scenario's which begin below break even obviously your expected outcome will always be below breakeven.
I'm thinking that since it's a fair coin, my path will be essentially a random walk through profit and loss. So if I do win the first trial, at some point in the future I'll be back to 1000 coins, and can effectively discount all the coin tosses in between, since the wins and the losses will be equal.
If I lose that first trial, or any trial when my balance is 1000, I'll lose 2 coins and 'waste' 2 wins getting back to even. Other than that everything seems equal, so it appears to me that this case, which will keep happening each time I cross from 1000 to 998, will result in me losing in the long run.
I agree that this is probably incorrect, but can't see the hole in my reasoning.
You can simulate your penny game rather easily in software using a random number generator. You have it flip trillions of times and try every possible betting combination you can think of. In the end total return would be 0 (+/- margin of error).
I will do. Here's a worked example of how I get 22 wins and only 20 losses, but break even:
balance results wins losses
1000
W,W,L,W,W,L,L,L 4 4
1000
L 0 1
998
W,L,L,W,W,L,W,W 5 3
1000
W,W,L,L 2 2
1000
L 0 1
998
W,W 2 0
1000
W,W,L,W,W,L,L,W,W,L,L,W,W,L,L,W,L,L 9 9
1000 -- --
22 20