As far as I know, every quadratic Hamiltonian can be diagonalised by a suitable basis change. Let me consider the basic squeezing Hamiltonian $$ H = \gamma (a^2+{a^\dagger}^2) $$ defined for the bosonic creation and annihilation operators $a$, $a^\dagger$. If I follow the standard approach of the Bogoliubov transformation, namely looking for a $b=u a + v a^\dagger$ such that $H=\omega b^\dagger b$, I obtain a system of equations containing $|u|^2+|v|^2=0$ which is meaningless.
(For details about the math you can look here https://physics.stackexchange.com/a/224301/160397 with $E+\Delta=0$.)
Where am I misunderstanding things? If every quadratic Hamiltonian can be diagonalised, and the way to do it is a Bogoliubov transformation, what is the problem here?
EDIT: this question is not about the math, as the underlying calculation is straightforward. The question can be expressed as: what is wrong with the Bogoliubov transformation here? Why is the transformation to diagonalise H not of that form?