I got two mage dwellings and Aislinn, while my opponent didn't get any. There's no point in describing the rest; it's clear what happened – lots of mages, lots of skeletons, lots of combat damage. No matter what, that starting position was impossible to win, even considering my own mistakes.
And the thing is, almost all the starting positions are like that. Here's a brief description:
1) Castle, two roads, one leading to a Garrison, the other to a Griffon Roost. No dwellings or money. I attacked, and lost 2 morale in the first round – restart. The opponent has 7 heroes on day 1 and a lot of roads.
2) Barbarian, one road to a Garrison, the other to a village. The village is blocked by 40 Goblins and 25 Elementals. No money, one Orc dwelling deep inside. The opponent has a Castle with a Stable, a couple of Outposts, and a lot of roads. I got lucky – restart due to incorrect road placement.
3) Tavern, one road to a Garrison (Mage Guild), the other to a village. No money, one Gremlin dwelling. Off-road, one direction is blocked by 80 Lizards, the other is a 5-day journey to nowhere. The opponent has 2 Wolf dwellings, 1 Goblin dwelling, some money, and roads. I only found this out on day 2, but the restart was still available on day 1. I was already about to give up, but the opponent took a restart with 113!!! I got lucky.
4) Rampart, the road to the village is blocked by 3 Guards with 6000 value each. No dwellings, not much money. The opponent has 3!!! Vampire dwellings, 2 Outposts. Restart due to a road that deviated from the starting point.
Finally, in this series of starting positions, something playable appeared, and the opponent didn't even take a restart (which they later regretted).
In other words, it was just a coin flip, and somehow it landed in my favor. And the skill factor has minimal influence here; in all these starting positions, there would have been a one-sided stomp even with a significant skill difference.