Two things that I've found that help a lot with the problem the author describes: Cloud hosting and YouTube.
We recently created some research software[1] that was somewhat kludgy to set up, and asked a high school student to give it a try. He got stuck on some early steps -- like working with the DVCS.
So we created a YouTube video[2] that walks through provisioning a new host on Digital Ocean, and each step after that. The video got him "un-stuck", and as a fallback he could always abandon what he was doing and simply replicate the entire video step-by-step.
We recently created some research software[1] that was somewhat kludgy to set up, and asked a high school student to give it a try. He got stuck on some early steps -- like working with the DVCS.
So we created a YouTube video[2] that walks through provisioning a new host on Digital Ocean, and each step after that. The video got him "un-stuck", and as a fallback he could always abandon what he was doing and simply replicate the entire video step-by-step.
1. https://sharps-ds2.atlassian.net
2. http://youtu.be/p54CCUEhfig