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The roof is original. Probably just been too long an interval since maintenance, so there is a fair bit to do.
Just like ours. I thought the pitched roof - which is the original - would need total replacement... but apparently not, just needs some new tiles here and there. Depending on how well it was put together 100 years ago, they can be pretty durable. Looks rough as fuck though.
Yes. Unless its sold as 'in fabulous just renovated condition'. Is the roof original? If not the fact that's damaged might indicate it wasn't done very well.
Possibly, see above. Depends on your position, how the sale has proceeded so far etc. You could float going halves on the repairs, that's what we did, which went down OK.
It's a massive ball ache to get anyone out to do any work on anything at the moment without throwing vast sums of cash at them, mind. Surveyor's estimates may be unrealistically low.