I'm trying to find some quick software to make a city map for a town I've made up for a campaign that I can send out to the players. Unfortunately I'm having absolutely zero luck finding software I like. The only thing that seems to fulfill what I'm looking for is City Designer 3 and that's $40 to get that on top of Campaign Cartographer 3 which is also $40; and I don't even know if it would work given that I've heard it's hard to use. There's lots of random city generators that create a city...but I have a specific shape and design in mind and hitting "generate" fifty thousand times is a waste of my time, I also want to annotate certain locations.
For reference, I want to make something like this but it can even less detailed:
posting cause i want to find a similar program but for making a world map.
Hexographer can make hex maps. I haven't used it yet, but I downloaded a free trial version when I was looking into something like this.
I have found a few options for making dungeon maps but not much for city or continent maps. Most of the time I scour the web for maps, then build my story to fit what I find 
Needing more flexibility I ended up getting the Cartographer3, 3-pack with Dungeon, City, and Overland for $99. So first, Yes, I find it kinda clunky and hard to use at times. It may have something to do with the sheer volume of options it has, or maybe there are a few things that are just made clunky. But in the end if you watch some of the tutorials on it, and make a few maps, it definitely gets easier. I guess it all depends on how fancy you wanna get. If you want to make basic maps that look decent, it's really not too bad. For me it's little things that just take time to get used to, all the layers and sheets that allow you to add effects to different parts, and the biggest hurdle for me is just the mouse interaction. It can be very tough to select something after you have placed it, and for most everything you can't just click and drag etc, you have to select it (which can be a challenge) then right click and select "Do It" from the menu which as someone that uses many Art and 3D animation programs, it just feels unnatural and clunky. The style sheets give you a massive amount of effects you can add from fades, to shadows, to glows, etc. It's powerful for customizing your map but with so many options it takes a lot of trial and error to figure out how to get the look you want.
But with all that said, if you just need basic maps it's fairly easy. As an example (if I can figure how to attach them), these are 2 I made for my current campaign, A world map and a small town, they are nothing super fancy or professional looking, but were not too hard. The Continent map took some time but the town took me less than an hour to whip up.
Just my 2cp..
From my experience over the last year: If you are only going to be making a couple of maps and sharing them with a small group, your best tool is paper, coloured pencils and a digital camera.
I remade the village of Phanelin in about fiteen minutes. Its taken me more than that just to get to grips with the basics of Hexographer.
A CAD-based product like Campaign Cartographer takes hours and hours of work just to get the basic skills.
The computer software is for people wha are going to be making lots of maps or who are going to be publishing them widely.
On the other hand, you should still try the digital tools. You might discover that you really like making maps. :-) It could lead to a new hobby or even a new career.