This is really a hit-and-miss, seeing as how nowadays I actively play on Medium (sudden shift in playing behaviour from end 3.6.9 onwards) but I frequently die so I do see Medium as really hard at times (my Forced Entry diatribe is a good example

) but yet I don't scale down to Easy/V. Easy because that was practically the only difficulty I chose in FS1... and I don't even remember the reason why I picked really easy difficulties in every game I played back then.
Heck, I doubt I even thought
anything about difficulty back then, like a robot on autopilot that always picks easy without thinking, just story, story, feel the story... LOL
It sounds like something suitable for AndroExe really (no offense intended). Or is he already on your cards?
Just curious about the whole thing since those conditions look kinda unorthodox to me.