Why don't hydride shifts occur with hydrohalogenation of 4-methyl-cyclohexene?
The reason for not having consecutive hydride shifts is that generally, a new carbocation is formed through shift only when it is more stable than the immediately previous one. 

To form a tertiary carbocation, 3 consecutive hydride shifts would have to occur consecutively (when + is at c-4 from the alkyl group, your first product) in which more than one intermediates have same stability (same number of alpha-H). Hydride shifts will not occur for your second product to form tertiary carbocation as the next intermediate is infact less stable (3 alpha-H as compared to 4 alpha-H previously).



Since the ring already has 6 members (least strain) so ring expansion/contraction will not occur either.