Reactions of differents halohydrins with tert-butoxide
Chair conformation RR-1 (shown as its alkoxides) is in equilibrium with conformation RR-2, which is the unfavorable partner owing to the strong 1,3-diaxial Me/alkoxide interaction. It is this conformation that leads to the epoxide 1. This route is possible if the rate of formation is much greater than the rate constant for RR-1 --> aldehyde 2. RR-1 has concentration on its side and anti-periplanar alignment of bonds for ring contraction. I prefer ring contraction but this does not preclude epoxide formation.
The RS isomer has two chair conformations, RS-1 and RS-2.  Again, RS-2 is an unfavorable conformation (vide supra) but has proper bond alignment for ring contraction. Conformation RS-1 has the necessary bond alignment for E2 elimination to form cyclohexanone 4 via the enol 3.
A priori, it is not easy to predict with certainty what the product distribution will be. The epoxide can only arise from the RR isomer while aldehyde 2 can arise from either bromohydrin. Organic chemistry is an experimental science.