I'm generalizing here. The air stairs deal seems to fall into two camps here. One is a group that thinks Cooper knew a lot about the stairs, particularly from secret info (CIA, Vietnam, Boeing etc). The other group thinks he only knew a little bit.
I'm in the group that thinks he knew some, but not a lot. One theory is that he could have simply flown on a 727 before and saw the flight attendants operate the stairs before taking off, then made an assumption that the stairs could be used in flight. He seemed like he knew what he was doing at first, but then not so much. Kind of like a guy seeing a home improvement video and thinking he can remodel his house. It's harder than it looks. He may have even talked to pilots or ground crew, we just don't know. There are 302s that have suspects at Elsinore asking about jumping, and one on a passenger plane in California (Burbank) claiming to be doing movie research.
I could argue both sides of this. Cooper did ask for the plane to fly low and slow, so that could indicate that he knew the stairs would be more likely to deploy if the plane was depressurized. If he was an aircrew member in the military, he may have seen planes fly with ladders down, doors open, with guys hanging out, etc.
The other side of me says that if he had never seen the 727 do this, then he was taking a huge risk that the stairs could cause air flow issues, or even make the plane unflyable. Or if they took off with the stairs down, do too much damage to the plane. Very risky on his part.
I hope we find out someday.