[quote=@Aristo]
[@Shorticus]
Quickie map tutorial now? :lol
I'm most interested in what might be the most mundane procedure: making the border outlines. I like to imagine I have a steady hand, but sometimes there are those 'I just can't' tedious moments when trying to make borders look naturally jagged.
[/quote]

As far as outlines go, it comes down to five things, really:

1. Practice.
2. Being willing to let tiny mistakes slide in the process. Nobody notices 'em.
3. Using terrain to help me decide how the borders should be shaped. The often form around rivers, mountains, and such things, though just as often you'll have some deviation from that rule IRL.
4. I favor brief, quick "strokes" with my mouse over longer lines.
5. I keep my left hand near CTRL-Z to undo my mistakes.

It's not a pretty process, but once you get quick with it it's easy. I use a mouse, though perhaps I should invest in a stylus or some shiznag.