Here's an idea on how to combat restarts during the aforementioned scenario:
A judge, who is not participating in the tournament, generates save files for most castle pairings and checks them for blocking situations and mandatory early encounters (further balancing is undesirable, in my opinion).
Consequently, the point of restarts disappears because save files where everything is too difficult can simply be rejected (although this is a drawback, as skill can never be improved without occasionally getting out of a tough spot, and it often happens that when you break free from a difficult situation and gain some space, you start to thrive).
As an alternative, there would be several (or a pack) of save files for each main castle pairing, and they would be distributed randomly.
I have some thoughts on the pros and cons of this idea (I think the cons are minor and insignificant), but I would like to hear what the community thinks.
The idea would be interesting, BUT the judge will simply burn out. Just for fun, try making about 10 decent generations of at least one castle pairing, say Rampart-Dungeon or Castle-Rampart, and you'll see. I've done such experiments and I'm sure it's almost impossible. At least, either this poor guy needs a lot of time and effort, or he'll do it without trying, and there will be no result. IMO, a huge drawback