What will be the Ozonolysis product?
There are two types of control, that governs reaction path: 


kinetic control (path with least activation energy) and 
thermodynamic control (path with least energy of products). 


Given temperature favors kinetic control. 

Ozonolysis starts as 2+3 electrocyclic addition (with later regroup of the product), similar to Diels-Alder reaction . Please, read about this reaction in good organic chemistry textbook, especially about what controls geometry of products, it will help to understand what I'm going to say next. 

Ozone has low energy of LUMO, so alkene part here provides HOMO, that is still lower then Ozone's LUMO. Oxygen from $OMe$ group donates some electronic density to $C-C$ double bound, so this bond becomes more active, then opposite one.