You could do it in Photoshop. You could do it in most things. I'd do it in Fireworks, but then I do just about everything in Fireworks. I don't know about Paint.net, but what you want is something with objects and layers and all that. That way you can move things around easy. Assuming you want this to be dynamic and repositionable.

Photoshop is huge, slow, and kind of an overkill for something akin to what you posted. Don't know about you, but I bothers me to no end to see a screen cluttered with a crapton of menus, buttons and options I know I'm never gonna need.
Paint.net is, in a nutshell, freeware Photoshop that mimics its versatility.

When you adjust/update tactical maps, you don't really need to draw objects all the time. Layers are immensely helpful, however. To give an example, when I make a location map, I use the following layers, from bottom to top: grid, buffer (for something that has to be temporarily taken away), spell effects, illumination/vision range, terrain1, terrain2 (details & additions to terrain1), objects (interactive stuff), agents (players & your mooks).

I do it in GraphicsGale, essentially MSPaint + layers + animation support (free version doesn't save to .gif and doesn't give you the full functionality of animating .gifs, but I doubt it's something you're asking for). It's simple and has a fully customizable key map.

Similarly, I'm biased here since I only do tactical maps and occasional crap pixel art and never used Photoshop extensively.
Yeah, way to undermine your own suggestion, AC.

You probably want a vector editor for something like that. Inkscape is free. Kind of sucks, but then what can you expect from open source?

Bob 2010/11/30(Tue)14:22 No. 10648 ID: 445c48
File 129115576569.png - (33.96KB , 741x223 , Herpderp.png )

>>10239
Yeah, I'm using Inkscape and it seems like exactly what I want, though I don't know how to do a bunch of stuff. Like on the arrows, in the OP pic it's kind of cut out, and that's neat, and means I don't have to recolor it each time. Not sure how to do that, so I've just used black. I also don't know how to make that sort of background.

Here's what I've got so far, for the riflemen circles. Looking at the OP, I might have to redo the arrow.

I've got two sets, One with a blockier feel and one that's more rough and drawn. Not quite sure which is better.

From Left to right, top row, Rifleman, Medic, Automatic Rifleman (Assault Stubber. Or maybe just a heavy stubber), Fireteam leader, Sniper, What's going to be a blockier flamer dude, Demolitions or grenade launcher or something, and what's going to be an alternate demolitions.

The furthest right is supposed to have a shadow effect but it doesn't save into pngs I guess.

Bob 2010/11/30(Tue)14:35 No. 10650 ID: 445c48
File 129115652583.gif - (1.23KB , 25x38 , icon_at.gif )

>>10648
Then again, looking at the originals, and the Light Anti-tank rifleman icon that I didn't even notice, I'm not quite sure I'm going the right direction with the last three. Those were designed by a friend, actually.

>>10648
So you want cut-out portions of a shape you say? Read the directions! (there's no shame if it's an open source product)
http://inkscape.org/doc/advanced/tutorial-advanced.html

look at [Subpaths and combining] and [Boolean operations]

>>10664
>Booleon operations

FUCKING YES. THAT IS WHAT I NEEDED.

I didn't even know there was a tutorial.

Oh damnit it stopped working.

Time to delve deeper into the tutorial to find out why.