Will multiple degrees (associate through a master in aviation maintenance) really help me in the future with my career progression?

Guess it depends on what you want in life, your goals, what you want to do after you get out - entirely up to you. Me, I attended Boise State University's Vo-Tec school, became a mechanic. Worked as a mechanic for a number of years. Worked as a professional guide. Moved to Denmark started my own business as a farrier shoeing horses. In December the wife told me I needed to stop as we don't need the money. So with no college degrees I was able to make a good living for my family. I retired from the Reserve as a SGM, got my SSI, my retirement planning has paid off. So the big word is "DEPENDS" on you, what you want.

They might open doors for you, but how far you go depends on your production.

You will always get two answers with the college question, the crowd without that never think college matters and the college grads that say college is important. Reality is somewhere in the middle. I do not need a college education for most of my nursing duties, starting IVs, passing medications, etc. You get good there with experience like in aviation. Now if I need to run the department and have a global view, those assessment skills in college and the ability to write and speak will come in handy. For top level success, you need both the technical and the college education. Your education will help you get the top-level interviews, your technician skills will help you keep the job for a long time.