Someone ought to post this in script requests
I'm honestly surprised someone hasn't yet made a script that will create 100 maps in the generator, and then assign x actors random names, random skills and such, and then also populates the database with random items, skills, enemies, troops, etc.
Then again, it would need some sort of logic to the names, else we will end up with the party of Ahaoghao h834tgh hagourgha and ahoya8g defeating a mighty ajg803t7g with 1 HP and 999 DEF.
As for the questions on a longer game. I'd start out making just the story, and use placeholders for the rest. Easy way to resolve this for fights is set all fights to have 1 HP and 1 in all stats. That way you (easily) win while you are testing the rest. Once the story develops, then work on the skills, items, weapons, armor etc. What I did was I started with the armors, set one set of armor as my base, then everything else was either an x% increase in DEF but a y% increase in cost of some sorts. For example, my heavy armor is 50% more DEF than the equivalent base armor, but you lose 40% of your AGL (as it would slow you down). So if you choose heavy armor in my game, you will take less damage, but go last in most battles due to the lower AGL.
Once I set my armors, then I set my weapons around them, keeping in mind what the defense stat of the characters would be for the armors at the same point in time. The items flowed from that, based on your HP at that point in time.
However, this needs the story set to work well, so you have an idea of when tier 1 items will be available, when tier 2 items are available, etc. If you don't set the story first, you will end up with what happened to me and your Dwarfs will be selling Elven weapons as that was the next tier of weapons and it was time for an upgrade.