Well big progress was made today. Negative pressure lip did almost nothing. Exhaust extensions did absolutely nothing. I did however, after no fewer than 5 sets of eyes looked at it, finally get a solution. While the red baffle seals are new and seal well against the cowl, the aluminum baffle plates themselves are just full of gaps. We sealed the easy ones with speed tape and even covered the lower 1/3 of cylinder 1 and 2 with speed tape and took it for a flight. It was 90° F outside and the CHT never got above 400° F this time. In cruise, it stabilized around 390° which is high but acceptable. I am confident that sealing the rest of the gaps and getting the airflow correct will bring things back to normal where they should be. It is to a point now that even as it is, I feel confident in taking it on trips. It will only get better from here.
Side note, my CHT probe is of the spark plug adapter type, which I’m told reads higher than a bayonet type. Perhaps something to change in the future.