I was a touch disappointed with the ending for the lack of closure on the secondary characters outside of the main four (Brian, Jenny, Ted, and Ki). However, I thought the open ending for those four was fine.
Jenny did end up like her mom in having a dream to be a professional gamer, but unlike her mom, she knew that competitive gaming came first in her life and she pursued it. Her mom selfishly started a family, then left them to pursue that dream. Jenny is 16 years old and perhaps, she will come back and be with Brian, but I think the writers wanted to really paint high school for what it is. You really love your first girlfriend in high school… then life happens. Maybe they’ll rekindle it after the summer.
Like you, I find BrianD’s skill confusing. Often, Brian is shown as an erratic player, being bad for little to no reason, but always finding temporary sources of inspiration that cause him to save the match at the end almost every time. However, at the end when they fight the Napalm N64 team, they are playing against the championship Napalm team plus professionals from the competitive gaming industry. Brian has little trouble killing these players and makes it to the end of the match, planting the game winning bomb. I would imagine that as he goes through VGHS and his skill progresses further, he will probably be offered a contract as well.
Of course, this then muddles up other things. Why was The Law not offered a contract if he was the best in the world, even appearing on talk shows at the start of the show? His death to Brian, which any gaming scout would see was completely self-caused and not due to skill, was so monumental, it caused Brian to be invited to VGHS. If Shane and Ashley were so good, why weren’t they ever courted to go pro?
I think you have to take this at face value. They can only fit so much into a web series like this. The rest is up to interpretation.
As far as the ending, many endings of successful shows these days aren’t happy ones. I find it cliche’ that the main character always has to die now because it sparks emotions and social discussions. Think about that, at least. They could be together one day. It’s open. At least they didn’t have Napalm hire a hit man and Brian jump in front of the bullet and die for Jenny or something forced and “emotion-provoking” like that.