3 D. Bo is OB, old boy (of a school, reversed/upset (a Down clue, set up), Rough is 'coarse' and English is language. I've never heard of Borough English, but assume it must be/was an inheritance system.
25 ITMA was an old radio show (It's That Man Again,maybe, I'm way too young!), about = reversed, with A (in the clue) inside. Amati, Italian family, so 'in Cremona'.