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If the map isn't too difficult, no one will probably spend time generating a starting save. I remember playing the Heroes of Might and Magic map "Devil in the Details." It's relatively challenging, but not extremely so. In that game, I had Caitlin as my main hero with a special ability that gave +350 gold. I bought her in the tavern at the very beginning to generate income, and I practically completed the entire map and all the battles with her, without paying much attention to her secondary skills. I only rolled 1000 gold at the start, and the rest was distributed somewhat evenly.
But on difficult maps, it's sometimes extremely desirable to get a good starting artifact or resources, or for the hero's skill tree to be suitable. It's not very pleasant to reach 20% of the way through a map and encounter an "unpleasant surprise" like some useless secondary skills. In that case, you have to experiment a bit even before starting the playthrough.
Also, I wanted to ask if anyone (besides Marlo, of course) has recently played Obi's newly released map, Burning Lands?