Understanding of the command line, delayed WYSIWYG feedback loop, FTPing/synchronizing files. Some generators don't even tackle "pretty, easy to install templates a la Wordpress" either.
All surmountable, but I haven't seen an "all in one, easy to use" fix yet.
I'd love if I could recommend a single client-side app for people to use that did it all. Something like Coda but tailored for beginners?
I'd be surprised if those same users could even manage to create a single, text-only post in most (pre-setup!) static generators.
Never underestimate agency. A working, ugly solution beats the hell out of a better solution that they can't understand.