Nick, when I was your age, my plan was to get my ratings and two year degree at Big Bend CC in Moses Lake, WA. Transfer to CWU's aviation program in Ellensburg, WA. Get a job at Cascade airlines in a Beech 99. And then get hired at Alaska or United.
Know what? I ended up at the local FBO and local CC for a two year general degree. Transfered to Riddle. Flew Grand Canyon tours, worked for the FAA, spotted fish, flew 135 freight, flew 121 freight, and got hired at UPS in 1990.
None of that was in my wildest dreams when I was 16.
My point? Be flexible. When your 16, you wanna have it all figured out, cut and dried, but that's not the way this industry works.
It's baby steps, man. Focus on your PPL right now, cause you can get that at 17. Worry about the rest, later.
By the way...a 757 is pretty easy to land. Especially if you let the autopilot do it....