I have been DMing since I was 9 and playing since I was 8. I have written several adventures but they were definately rough. In general I’ve been told that my best sessions are the ones where I play it off the cuff with little or no direction. I find my sessions tend to be much the way my short stories do, I start out pointing in a general direction and they write themselves better than I ever could have planned.
My games have almost exclusively been ran with close friends, relatives and their close friends. Haven’t put myself out there for a convention game or other setting like Pathfinder Society but it is my plan to do so before long.
One reason I am looking into running a game via obsidian is that I write SO much better than I speak. I tend to get nervous in front of groups of strangers but I have ran some exceptional chat adventures with complete strangers. Therefore, this seems like the write medium to run such an adventure.