Aromaticity------->Resonance -------------->Hyper Conjugation ---------------->Inductive Effect.
This the trend to Check the stability of a Carbocation.{Because carbocation shows all the effect}
for free radical you Go through resonance and Hyper conjugation.
For Carbo anion You check only by Aromaticity,Resonance,Inductive effect.{Because hyper conjugation is not the property of Carbo Anion}
Now in your question Intermediate will be two compound (Normal pentene) with + on the third carbon and and second one will be with positive on second carbon. and.
Now the Major product will be by the intermediate having stable carbocation.The intermediate compound do not show Resonance,and Aromaticity.So,now you will check its stability By Hyper Conjugation Or by Inductive Effect..
Hence in the previous case we have the same situation so considering I.E we have MAJOR product 3-bromopentane
Note: In the case when you are finding the stability of a compound and if the compound shows both effect Hyper Conjugation and I.E then I.E will dominant if the -i.e group is attached otherwise...hyper conjugation.