For me the biggest hurdle by far is deployment. It's honestly impossible to describe how much of a gulf there is between those who see it as a completely trivial matter and to those who don't know what's going on.
What part of the deployment process are you having difficulty with?
I want a tutorial that starts with "You want an app to do X with your friends, like an imitation of Doodle for planning Dungeons and Dragons sessions? The real way? Set aside $X money/month, book a domain name, and we're going to set up a real website, incrementally, and publicly available at every step along the way."
Stuff like Heroku people make sound like it's a one stop shop but it feels like it hides too much and you don't have access to your files like you do in your desktop. It's an environment conducing to pushing out stuff quick, not learning.