Given the moduli space of hyperplanes in projective space, V. Alexeev constructed a family of compactifications parametrizing stable hyperplane arrangements with respect to given weights. In particular, there is a toric compactification that generalizes the Losev–Manin compactification for the moduli of points on the line. We study the first natural wall crossing that modifies this compactification into a non-toric one by varying the weights. In particular, we prove that in dimensions two the wall crossing corresponds to blowing up at the identity of the generalized Losev–Manin space. As an application, we show that any Q-factorialization of this blow-up is not a Mori dream space for a sufficiently high number of lines. This is joint work in progress with Patricio Gallardo.