Questions about managing own server
Ning To Jamroom
Similar to you I don't know enough about servers to run one entirely from the command line. It's not so much the command line, I just don't know what to read to keep myself sufficiently informed in order to remain up to date.
So I "outsource" that to webmin/virtualmin (free software with free docs, roughly equivalent to whm/cpanel), and rely on their expertise. There is a learning curve, but the gui and the help and the emails when you need to update are extremely helpful to me and make it possible (for me) to attempt a non-critical unmanaged server or two.
After reading the virtualmin docs and doing a few installs, if you have any doubts at all just go managed until you have confidence in your ability to run it long-term.
updated by @ultrajam: 01/19/15 01:45:07PM