You're right in that it depends what you want to do. Programs like Inkarnate, Wonderdraft, CC3 are incredibly easy to learn and work with. But what you see is what you get. I've seen so many of these maps and they start to look very similar. If you love the art style in any of those programs and you're not into struggling up a learning curve for a more robust program, save yourself the headache and just use them. I've used Inkarnate for some projects and I've been happy with it. It's great for what it is. For another map I'm working on, I want it to look like some of the great maps I've seen on this guild and for that, I need Photoshop. I have no artistic ability and started from zero in terms of PS learning curve so it's been incredibly frustrating and I get into cycles where I get over a hump but then run into another hurdle and just abandoned it for months and then come back to it. So yeah....it depends what your goal is. I recommend you take a look at the finished maps on here to get an idea of what you're going for. Then find out how those maps were made and back into the software from there.