As a 15W in the NG, will I have enough experience to get a contractor job right out of AIT?

That all depends on the company you work for. Some require you to have a bachelors degree and be IO qualified. I'm sure you can find a job operating shadows in the civilian sector, just gonna have to look. Ask some of your civilian instructors, they can help a lot

Very doubtful without a couple yrs experience. Get as many launch and recoveries as possible.

You'll need a couple of years under your belt if you want a real shot at a contractor job it's a great experience and all but you'll need yrs under your belt if you want to go to a good contractor job as a uas operator