For number 2 it depends on strategy. The strategy you outlined has you risk $5 to win $1000. Of course in a fair game you will go broke most of the time. For every time you win you should lose 200 times to come out even. But you can easily take the reverse strategy. Bet $5 if you win, leave. If you lose double your bet, if you go down $1000 dollars leave. In this case you are almost guaranteed to win. But the times you do lose you lose enough to make up for all of your wins.
EV is EV, it doesn't change based on who has the larger bankroll. The casino doesn't magically get an edge because they have more money. They get the edge because the game odds are in their favor.