By the time I was in high school, I had a pretty decent amount of coins saved up. But in all reality, they probably didn't amount to anything substantial. Just stuff I came across in change and some simple coins given to me by my parents that they got in their change or tips. The one coin in particular that I do remember was an 1808 half dollar that was very worn that I had purchased from a friend of mine when I was a freshman in high school for either $15 or $20 dollars. I got my very first girlfriend in high school. I gave her my entire collection in a little wooden treasure chest and told her to hold onto it for when we get married and have a family. Not sure how long that lasted but a year later, we were broken up and when I asked she told me that her little brother stole them from her at some earlier point in time. Apparently he had sold them over a short period of time for drug money. Oh well, lessons learned.
An 1838 Half Dime that I bought from my mother's cleaning lady in 1959. I cleaned it when I was kid and improperly stored it in an envelope with sulfur in the paper. It is not a very good coin anyway, so no harm done.
I think my first I really cared about was a 1865 2cent I bought off a friend of my father’s. Another early purchase was a 1817 15 stars large cent. A bit crusty but nice. I was constantly selling and swapping stuff so I don’t remember what happened. I think the 1817 and the 1800/179 large cent I really treasured got lost in the move when I was 12. I got back into it at about 16. And I bought this then was of course raw. I think I paid $35. Through a mail order ad.