Addition of HBr to Vinyl bromide
The reaction of $\ce{HBr}$ with olefins is a relatively fast reaction, in other words, the activation energy required is small.  Further, formation of the carbocation intermediate is the rate determining (slow) step in the overall process.  Considering both of these facts and applying the Hammond postulate we can say that the transition state leading from the reactants to the carbocation intermediate will be an early transition state, it will look more like the reactants than the carbocation.

This suggests that resonance and inductive effects need to be examined with regard to the reactants, rather than the transition state, in order to determine how the molecule will react with an electrophile (the proton).



As the above diagram illustrates, both resonance and inductive effects (in an early transition state that resembles the reactant) suggest that the beta carbon will be more nucleophilic than the alpha carbon.  Therefore addition of the proton (electrophile) will occur at the beta carbon.  This will be followed by rapid addition of $\ce{Br^{-}}$ at the carbon already bearing a bromine atom (the alpha carbon) to yield a geminal dibromide.