10 years isn't long enough, but with the "starting over" theme my biggest change would be to not take on the debt loan that I did; I'm fortunate that I've been able to support the payments and still live comfortably but it (among other decisions) has made it difficult to invest in things like a family and housing.

Education wise I likely would not have done grad school right away, at the time a 5th year masters was appealing but the shiny paper didn't really end up doing anything for my career. I enjoyed the work but I would rather have had an employer pay for it. On the flip side a PhD would appealing since I do enjoy the research process, and there are some areas in the aerospace field I would love to explore more deeply. I would likely do CS instead of AE/ME, I originally picked this field because I love aviation, but career wise I've found myself enjoying CS work much more.

I would more strongly consider ROTC; I rejections from military academies and decided to go to the university route instead (aviation generally requires a degree). I still greatly enjoy aviation but I'm not in a place financially to pursue it.