Hello Gibbo, good to see you on the forum.
Thank you for writing up your experience. If possible, can you incorporate some of your comments and improve the Wiki
https://www.snakeoil-os.net/wiki/Main_Page
Many of us have been using things for so long that we have forgotten some basic things. So, a fresh set of eyes will definitely help improve the Wiki.
I suspect your timeout issues are Pi/Raspian related. I am using WinSCP with my Intel NUC/Ubuntu and have not come across the issue. There should be no need for you to know your Linux commands at initial install. However, please add to install Wiki the commands that may be useful for others to know.
Please explain further what you mean on basic configuration. Is SnakeOil not doing something that it should?
I agree that mounting music library experience can be improved. Perhaps this is something that Agent Kith can include in new GUI which is the next release.
Please start a separate thread on LMS. I assume you have logged into MySqueezebox first. LMS uses ALSA, same as mpd, so it puzzling that it works with one and not the other.
I do not use mympd, so someone else can answer your question.