Worried about difficulty in getting transcript(s)

It’s been 16 years since I graduated high school, and a college in New Hampshire I spent a semester at back then has since closed. I am a veteran transfer student with about 18 credits of college course work in community college, now transferring to some top private schools.

My problem is, with that closed school transcript, NH charges $20 PER copy, so if I wanted to apply to 5 schools I’d be paying $$$. So I guess my question is, when I fill out the common app, can that just be uploaded to my profile there and be there forever so I never have to request it again? It would be nice to have them all in one place so you don’t have to keep requesting them every time you apply to a school.

Another question I have is, do colleges like reading unconventional experience, written well, for example being homeless for a short time and how that shaped the course of my life, or are they only interested in academic clubs and athletics?