This is a fantastic thread, and I would love to get in on the discussion! I can't at the moment, but I'm posting here so I remember to come back later. I'm starting a web series as well, so I can definitely relate to a lot of this.
A couple quick things to add, I suppose. I can see both sides of the "luck" debate, though I'm leaning more towards luck sometimes being a factor. Not every time, but I do believe that sometimes you can have two shows of equal quality and one goes by the wayside and the other just happens to get shared at the right time, leading to more views, leading to another lucky share, then another, etc. Luck won't make a bad show popular, but I do believe that every once in a while an otherwise unknown production can gain popularity through a happy chance. Even just striking on one video that becomes viral can take luck. There are plenty of viral videos out there that were floating around for years before getting shared in just the right place and catching on. People often don't know they're hitting on something big when they do it--they were just making what they wanted to make. That feels like luck to me. But while the concept exists, I suppose I don't feel it's necessary to success.
As for the "no room for originality" thing, that's kind of a tough one. On the one hand, Youtube is a powerful platform for people to do what they want, and sometimes what they're doing is original. But on the other hand, sometimes I look around and it really doesn't seem like there
is room for creativity. Even the good-quality stuff is still following certain formulas. Glove and Boots is great, and they've got some really funny sketches. But their sketches aren't what made them popular. What made them popular were extremely shareable lists and videos about current pop culture stuff. The sort of thing that people share on Facebook. Now sometimes it feels like that's all they do, because that's the stuff that people tend to share--not just videos that are funny. Similarly, it seems like the kids content that's popular on Youtube isn't particularly creative or original--it's just highly polished and easily sharable. That doesn't mean that an original production can't succeed, but I do believe that people tend to like what's easy and comfortable, and what refers to pop culture that they know about. It's frustrating, but that doesn't mean I'll ever stop doing what I feel is good, and hunting for an audience. I know they're out there; they just might be harder to find because they represent a smaller part of the population.
Well look at that, I made fairly long post after all. But those aren't even my real points! I'll be back to share my experience and thoughts on making a show!