MrMarcus, let me put the question back to you.
You wrote: "If a coin is flipped 100 times and comes up heads 55 times, then flipping that same coin 100,000 times will result in 55,000 heads."
Ok. So if a coin is flipped 100 times and comes up heads 55 times, what would make 100,000 coin flips result in a 50-50 distribution? Can you guarantee a 50-50 distribution? Of course you can't.
Therefore, a gambler with an 80K bankroll who loses $300 on the first session of play can not guarantee or even assume that he will break even or come out ahead on the next session. Can he?
So, how many $300 per session losses can a gambler with an $80K bankroll endure? About 266.
What the math cannot predict is when you will have a win.