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#4
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then it becomes a dead end.
Let's say you bought the Tome of Shadows. With such a poor starting point for the main character, it's unlikely you'll be able to defeat the Barbarian, even if you spend months collecting artifacts and squires.

But let's say you did defeat him; there's a dead end – behind him is another garrison, just as strong as the Barbarian's army. Let's say you defeat him too, but there's no way out?
You'll have to replay (or place a portal outside the garrison to leave), or can you choose any garrison?

Regarding making it more difficult, it's questionable whether that's necessary. You have to replay it many times to get the Chalice of Ents with a level 30 hero with minimal losses. It's small, with 60 archers and 30 simple dendrites.
The Executioners at the tent are a whole other story; the guard is mediocre, and the losses are noticeable compared to their small army.

+Druids at the arena; it took many attempts to get it with the loss of only 1 peasant, and usually, you lose griffins and a couple of squires.
And the witches at the Guild Fortress also don't have a weak guard, considering the newbie main character and the small army.