You're moving in the right direction, and your skills are getting better, but like you said there is still a lot to be done.
The "men" look better, but there is some inconsistency with them, from a uniform perspective. Morales, Duque, Romero all look different. It might be better to use the same guy, but flip and rotate, etc. to make the differences.
I think the legend flags/backgrounds need to be a little lighter and more in the background, possibly lighten the opacity. I also think you can find a good old-time font that fits a little better, and compliments the "Remember the Alamo" text.
Possibly think about lightening the territory borders. It's a little chaotic to my eyes with all of the lines. Good use of the Path Tool it looks like, but keep all of places they touch nice and tight. ex. where DC3, DC4, and Crocket meet.
It took me a little while to figure out where the Chapel, Saloon, and Covent Yard were. You need to explain that better, poss. change the legend to include something like Chapel (CH) +1, Saloon (SA) +1, etc. Along those lines it's not really obvious who the generals are, so you'll need to work on that.
For me, as for your questions, just keep working on them all. There is a lot you can do with this map. Keep up the hard work.