Knowing all the facts, does it seem just to sentence Bob to four years in jail and James to five years in jail?

You answered 'No'. That's right.  A judge can assume that the community in general would consider it appropriate to punish a repeat offender more severely than a first offender.  However justice also requires that the sentences imposed should not be unduly harsh when measured against community values and expectations.

On the facts given in the case study, it would seem that sentences of four and five years are at the higher end of the available penalties. But the value of the stolen goods in this case is small ($100).  The fact of breaking into a house makes the case more serious, but it is not the worst sort of case that might be imagined.  Taking account of the maximum possible penalty (five years) for the worst cases of theft, it is reasonable to suppose that the general community would expect this case to attract less severe penalties.