First senario:
The 1000$ you already game me are irrelevant as I keep them either way - I put them in my pocket. Then I have the choice between getting 500$, or getting 500$ on average. It is the same as if you gave me 500$ and asked me to flip a coin for double or nothing.
The big question is are we playing this once or many times? If we play once, it depends if this punk feels lucky. If we play many times, I gamble and wait for a highly probable fluctuation threshold before quiting - play the variance.
Second:
I assume I have to choose one of the two? In that case it is again equivalent to giving me 500$ and playing double or nothing. Again, since I cannot go to negative profit here, if we play many times, set a highly probable limit for a fluctuation and quit once you hit it.