EDIT:
maybe I should've spoken up about my map painting program I made years ago (if I still have it)?
I'm interested in this program too. Wanna post it if you can find it?
It requires small photos I had with it. Also it's squares, but with some tweaking, it MIGHT be able to do hex. It makes a sizeable area of your choice and you hit a key to change the value and image to what you want.
I had water as 0 and default, plains as 1, mountains as 2, sand (coast/desert) as 3, hills as 4. It was a final project for a game I was making based off of (unknowingly) a D20 game like D&D. Everything was based off of a D20 except enemy encounters which was a percentage per area per step. So you could be fighting slimed for an hour and a wyvern shows up and ruins your day (3/100 chance to get). As
Chaotic as it was, the weapons and skills were all implemented for 3 classes: fighter, rogue and Mage. Each branched off to one of two subclasses, fighter had knight and mercenary, assassin and thief for rogue, and summoner and wizard for Mage. Each one had like two skills and one broken skill, like the summoner had one skill that was a random monster of 20 and if you got like 15+ you decimated enemies, 10-14 were buffs, 5-9 was a deal extra damage and 2-4 was a prevent all damage type thing and 1 was a damage everyone relative to their defence (more for high defence, less for low) and then remove all defences of all combatants (so very suicidal but great).
From just that alone, you can tell it was too big to finish alone in 2 months