Personally I'd rather spend my time in the building with large windows and tons of natural light than holed up in that dark old castle thing.
That prison building is overly stylized to my taste. And given how complex the exterior is and seeing it's state it's obvious it's hard to maintain. Unless you like all the gunk growing all over the building all the time.
Is the old building "fancy"? Sure. So is that fragile china that's kept in the fancy vitrine but rarely actually used because it's such a pain to maintain and actually use.
Then you're part of the 20% of people who prefer modern styles, for whom 99% of buildings are built. You have plenty of choices, while the rest of us are lied to about why buildings look like they do and why we can't have what we want.
I think the prison looks better from the outside, but if you asked me which building I wanted to spend time in I'd pick the school without hesitation (assuming they were both being repurposed for the same non-school/prison use).
There is a clear preference for other people to build in traditional styles, but as soon as you have to care about more than what the facade looks like from the outside people choose the uglier functional option.
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