In the comics, sure, but the movies aren't the comics. In fact I find Jessica Drew to be even less likely than Monica or Kamala because despite being her best friend, she's largely tied to a completely different mythology.
They aren't going to have Jessica Drew as some major character because that'd require delving into a bunch of completely different, likely unrelated stuff about HYDRA and her family, none of which serves a Captain Marvel movie. Save Jessica for her own movie or TV show.
Whereas Monica would be easy to slot in as a friend or comrade without having to do a whole huge origin story or unrelated plot.
Tony Stark wasn't a very likable person either. MCU Tony Stark is way better. In the comics, he comes across as darker and more serious than his MCU counterpart. The movies are not the comics, true. Every movie so far has gotten the supporting right. Sure, the relationships may be different, but in an Iron Man movie, you still have Pepper, Rhodey. Sure, the relationships may be different, but all the right characters and there.
I would love to see a Jessica Drew movie, but there is no reason why she can't show up in Carol's movie first. Remember, Black Panther is showing up in Civil War. So long as they don't give her too much exposure before her solo film, would they risk going the way of Black Widow.
No more than going from the Air Force to SWORD. People forget that Carol wasn't a SWORD member in the comics either.
Actually, it's not. Not at all, especially with Carol's background as a pilot. NASA only takes the best pilots to be astronauts. On top of that, The Air Foce is more closely connected with space operations than any other service. Ever heard of Air Force Space Command? I guarantee you they don't have that equivalent for the Coast Guard.
The idea of Carol working for Sword was most likely popularized by her first appearance in The animated series Avengers: EMH. They could very well have Carol work for Sword in the movie, or just replace it with NASA, which was part of Carol's origin in the comics anyways.
She's a character who was inspired by Carol and who uses a codename that is a variation of hers. That's absolutely a connection even if they don't meet face to face.
All it really takes is a scene of Carol rescuing a little girl and then revealing her name is Kamala.
That could work, but that would majorly suck if I see Kamala and Monica, but no Jessica Drew in a Captain Marvel movie.