The first two maps are by Mike Schley. I think the buildings are laid out with City Designer - a plug in for Campaign Cartographer - but I'm not certain. All of the rest is done by hand in Photoshop. I know you don't like it, but Gimp is the best free program to use to get a close approximation of photoshop. You'd need a tablet to be able to use a similar hand drawn style. Another option is to draw the lines by hand with a good black ballpoint and then scan or digitally photograph them to make them digital. Then it's easier to colour them in Gimp.

Soldier on with the tutorials. There are many tutorials here on Gimp and other programs. Once you've got something, post it here and sa what you don't like about it. Then we'll help you fix those bits until you have a result that you like.