I totally disagree with the idea that skating alone is a better way to progress. I've always found that having other people to skate with, whether they're my friends or just random people are a park or spot, makes for a better session for me. Seeing other people land their tricks motivates me to land my own. Even now when I typically always skate alone, I'll land tricks I haven't landed in years if one of my friends comes out with me because I'm hyped to have someone else there.
I've never been good, but I was at my best when I was in my early 20's. No real responsibilities, no relationships, tons of free time. I started when I was 12, so it took a good 10 years to get that very limited bag of tricks and that amount of comfort on the board, but it was a steady progression up to that point. I'm 30 now and have all the stereotypical adult responsibilities (job/wife/kid/house) and making time for skating is harder, but it's still just as fun. One of the best things in life that I've learned is that you don't have to be good at something to enjoy doing it. Probably doesn't apply to all things, I wouldn't say go practice surgery if you didn't get into med school, but not being a great skater shouldn't discourage you from having a good time on your board.
My advice for progressing is to skate with people who are better than you and try to skate what they skate if it's within your reach and skate different things. You might surprise yourself with how well you skate tranny if you've never tried, or rails, or gaps or whatever. And just skate often. The things that are hard now will become easy the more you do them.