I tried skating back in middle school and high school. Sadly, I was too chicken to really try anything, with my “most daring” thing being dropping in on a 5-foot 1/4 pipe…it was actually kind of scary and only successfully dropped in once before getting too confident to try again and hurt myself. I also was able to ollie a deck on its side. Other than that, I didn’t take it very far and kept it simple with hopping on and off curbs, grinding curbs.
I switched to just cruising longboards as I got older…no steep hills, just simple cruising as I found it relaxing. I currently have a pennyboard, nickelboard, and a G-bomb cruiser that lets you adjust the angle of the trucks for either hard carving or stability.