Dimethylene Cyclohexane to Octalin-1,4-Dione | Hydroboration vs. Ozonolysis Pros Cons
Comparison of the two approaches as far as yield/cost/etc. is void because one of them does not provide the same product as the other. Hydroboration-oxidation of 1,4-dimethylenecyclohexane yields 1,4-bis(hydroxymethyl)cyclohexane with undergoes oxidation to yield 1,4-cyclohexanedicarbaldehyde or 1,4-cyclohexanedicarboxylic acid.

Now, you may be able to take the carbocylic acid, covert to acid halide and then react with $\ce{LiCuMe2}$ to get the ketone, which should undergo Baeyer-Villager oxidation followed by hydrolysis to give the alcohol you want. Or you could covert the diacid to the diamide and subject it to Hofmann degradation to get the amines, which you might be able to convert to the diazo salt with HONO, which may hydrolyze to give the desired diol. Both routes ae significantly more convoluted than ozonolysis, which decreases oveall yield and increases cost.
Now, there are other oxidative cleavage reactions which might be cheaper.