It is extremely misleading to look at it that way. You are not doing yourself a favor.
It is 'fatally wrong' to look at it from that perspective, simply because there is no way that you will play and succeed in winning ONE UNIT and quit for the day.
You will restart your series of wagers many times. Perhaps as many as 50, 75, or 100 times over the course of your session. So many times that, in fact, you quickly become a favorite to go "belly up" within one or two sessions.
Think about it. For simplicity's sake let's say that you have deep pockets, a high limit table game, and nerves of steel. We will assume that once in a hundred times you will fail to finalize your series of bets with a win. As you are positing a success rate of 99%, that means an expected failure rate of 1%, which means that if you play the series of progressive bets just 100 times, you are "even money" to "go broke".
This is essentially what happens with all progressive betting schemes; and it is why the casino will gladly let you right down your results as you play in order to keep track of your progressions or regressions, etc. Indeed, if you are playing for high enough stakes the casino will certainly send a limo for you; as they have done for nearly a century for the hundreds of thousands of suckers before you who have had the same or similar not-quite-accurate notion that the casinos are charitable foundations that are itching to give you their money.
Your figures are off. Way off. In real life, your winning sessions will greatly outnumber your extremely rare losing session so that the overall chances of you ending up ahead are quite high. If you win $10 99 times and lose $100 once, you are well ahead. Can you lose your $100 two, three or even four times in a row? Absolutely, but the chances are about the same as hitting a serious lotto prize.