I've been skating an indoor ramp by myself for the last 1.5 years, and only recently have been skating with friends and other skateboarders on a more regular basis. It feels good. Last session I did the best mini-ramp line I've ever done, which was still super basic and could've been cleaned up, but I was hyped.
Also not a session, but I plan to skate every day that I can this year, which is looking like five+ days a week. I just don't want to get seriously injured, so I have to take calculated risks and be smart about what I'm trying, plan ahead a little, etc.