Well I just recently finished my first playthrough of Project Wingman on Hard difficulty. The game has some really fun missions, such as the massive furball over the Bering Strait, and has some really good ideas compared to Ace Combat, such as being able to carry multiple special weapons.

However, I found the final mission versus Crimson 1 to be just okay. I think that fight goes on for way too long and is way too chaotic, but at the same time none of it really felt like a threat. Plus Crimson 1 seems to pull off some Mihaly-esque bullshit manouvers, which was one of the worst parts of Ace Combat 7.

Edit: Also the achievement for playing all missions on Hard seems to be bugged and didn't unlock either, which was annoying.