I suck at making D&D maps and it makes me sad.
I've tried a couple of programs, and they are easy enough to use, but my maps always look terrible to me. I hem and haw over how much forest, or how many villages, or other stuff that probably doesn't matter all that much in the long run. These elements, however, form a series of mental blocks that cause me to throw my hands in the air in defeat.
An alternate method, and one I used to use back when I ran Stars Without Number, is to generate them randomly. (My generator of choice is Wizardawn) Of late, however, I don't feel a connection to a map I generate randomly, it's not "mine." I don't know why this wasn't a problem back in the day. (Probably because I was gearing up for grad school and I didn't have time to let things like that bother me.)
I'm going to make another attempt tonight with Hex Kit, a program I got in the hugediculous bundle hosted on itch.io earlier this month. The program itself is not complicated or difficult to use... I just hate the maps that I make.
I don't recall this being such a problem when I was a kid, or even in college. Perhaps it's because I didn't have the exposure to map making greats like Dyson Logos and Niklas Wistedt. Maybe I have the map-making equivalent of the mindset that some people have where they think they can't DM because their game isn't like /\/\att /\/\ercer. (That's a whole other can of worms I'm not going to open up.)
I'll give it a last shot, and if I hate them then fuck it, I guess we'll use the Known World or something.