---

I have a 1989 22' cuddy and the reason you could not sit as you describe is that the cabin stops where the deck drops lower. You can sit on the forward V benches without ducking, but the "floor " in the cabin is too narrow for a chair.
I looked at Mills site and there are several pics of 22' with forward shelter. I appears to be at least 1' higher than my cuddy, maybe even more. Looks to be at least as high as the console top surface.

I just looked at 22' outrage photos, pretty sure it is Joe's boat on a trailer. The cuddy is as high as the console top and probably almost the same as the shelter. The shelter comes further to the stern and would possibly allow your desired seating possibility.
My boat is 50 miles away or I would measure it.

In my inspection of the cuddy installation, it is simply a molded fiberglass piece that is screwed to a 22' Outrage open. I am personally very happy I chose what I have. The seller had one of each and was selling one and keeping one. I got my choice and have not regretted it.