First off, winning 65% of the times on -165 is too optimistic, it's profitable on it's own with the same wager each time so if you were hitting -165 at that rate you should be pretty rich and not try chase system but we can use it if you want to for our calculations.
I also consider that the events are independent of each other; Greinke doesn't lose many games in a row but really, his starts are independent of the previous ones.
The chance of losing each bet is 35% (100%-65%). That means that a chance of losing 5 bets in a row is: .35x.35x.35x.35x.35= .52%.
Therefore, a chance of not losing 5 in a row is 99.48%. So if your bankrupt point is after 5 losses, each time you play, you have 99.48% chance of not going bankrupt. Now the kicker is that the probability of you going bankrupt increases every time so we calculate that in the same way as before. .9948x.9948x.9948x.9948 etc. 8 - 95.9%, 16 - 92%, 32 - 84.6%, 64-71.63%, 128 - 51.3%. So if you repeat this system 128 times you have close to 50% chance of going bankrupt. If you go through one "cycle" once a week you would have a 50% probability of going bankrupt in a little over two years. Most people play more often because you usually have a winning ticket on 1st-3rd try and if you are playing one game a day you should be going through 128 cycles in one year (going bankrupt in one year).
If you take 63% winning percentage (more realistic, still profitable at -165 odds btw); the numbers get much scarier in the long run. x.37x.37... = .69% chance of losing 5 in a row. 99.31% chance of not losing 5 in a row. .9931x.9931 etc. 8 - 94.6%, 16 - 89.5, 32 - 80.1%, 64 - 64.2%, 128 - 41.2%. So 59.8% chance of going bankrupt within 128 cycles.
I don't have time to go through the wagers and how much you have to wager to have $50 profit but the first calculation should show you that it's a doomed system and most people realize it when it's too late and those who tell you that it's a great system is because they didn't get to the bankrupt point; they either didn't bet the system long enough or were lucky/made great picks but the probability teaches us that you will go bankrupt at some point in the future. So you can play it for awhile and probably be fine but I personally don't even like to play it 15 times for example because the idea that there is 10% chance of me losing the whole bankroll is too scary and as said before payouts are not that great. BOL hopefully i explained this correctly and my math is right