Do conjugated double bonds take priority over a +1 formal charge?
Given the symmetry of this benzyl cation, the "direction" does not matter. I have put direction in quotes because there actually is no such thing. Electron pushing arrows are a helpful tool (at the very least for accounting purposes), but it is not what is happening in this molecule (or most other cases, either). What you have here is a resonance structure, meaning that the true situation is not well modeled by a single Lewis structure, thus we use several, and the true situation is somewhere in between the structures with varying contributions from the individual ones. So it does not matter how one arrives at these structures, it is important that they be reasonable and do contribute.

One could argue that the answer given is more extensive than your attempt, but I would consider both equal. The reactivity of the molecule is not dominated by the aromatic ring, thus placing extra emphasis on it seems superfluous.