I hate to draw the USA. USA is relatively simple, but you have to draw each star separately instead of little dots, and he's very common to draw.
Aside from that, I draw OC countryballs on NationStates and my flag is pretty damn difficult.
I use Verdana in most of my comics, except for those odd occasions in contests when I want to conceal my artstyle a little and go for something else. I've considered switching to the Nunito Sans family in the past since I used it not long ago when I redid my CV from scratch.
Most of the sans serif fonts are good anyway (except for Comic Sans of course).
Same here. You get used to its idiosyncrasies over time, but if you're not planning on using it for a long time (>1 month) then I'd advice use to check out Medibeng Paint.