Yea man ... But I'm contemplating on how I am going to continue to do it.
Trying to decide whether or not to keep betting what I previously won, or keep starting over at 100 after every 100 I make, so that I don't take one bad beat, and lose it all.
I wouldn't go that route. Just use confidence points and increase your bets accordingly.
"Is there any reasonable chance that [team x] loses this game"?
"If they played 100 times, would underdog [team y] even win 5 games"?
Just keeping asking questions like this. Let the answers guide you.
At some point you'll take a bad beat. Just know that it will happen. And it's for that reason that people think betting on the ML is risky. I look at it a different way. Betting on the ML is safe because I'm winning all my games. And so I'm continuing to accumulate money and increase my bankroll such that a bad beat isn't really all that bad.
Sometimes you have to be willing to pull the trigger on a play for an amount you're not comfortable with.
You think I didn't have reservations about putting 300 dollars on Serena Williams at -900? But that's fear talking. That's not your rationale. Your rational brain knows Serena is going to win 6-0, 6-1 in about 25 minutes, and so you make the play.