Some of those dated expiry price prints are latent artifacts when you’re looking at a price ticker - don’t read too much into singular month anomalies.
I’m not sure yet I necessarily agree with the notion that you’ll make money in Backwardation for your particular circumstance as a function of roll yield.
Your outright flat price risk is far far greater than roll yield risk if I understand your position correctly. If you roll August into a far dated expiry just understand that the dated expiries typically have a more muted trading range as compared to the prompt month.
I think I'll just roll it over to the next month. I guess that is how it's normally done. How long before the last trading day do people typically wait to roll over?