The problem I have with this cartoon (and the concept of white privilege in general) is that it isn't really clear in the examples whether the person is benefiting from racism, or merely having the kind of opportunities in life they might be expected to have whether or not racism existed. Take the example of the mortgage loan - if that's an example of a benefit from racism - then the person COULDN'T have gotten a mortgage loan without racism - otherwise the relationship between getting the loan and racism is coincidental rather than causally related. The same with a career - if having a career is a benefit of racism, then it would not be possible for Bob or any of his family to have a career without racism.
This leads to the conclusion that IF Bob has benefited from racism, and the situation were righted, ideally he or his descendants would be unemployed, homeless or living in substandard housing, or in jail.
Against that, you could argue that Bob and his family have simply had the kind of rights (not privileges) that any decent society owes all it citizenry, whereas the black characters in the cartoon have been denied those rights due to racism. If you regard having access to decent housing, careers, equitable treatment from the police, and so forth, as PRIVILEGES, then if follows that not everybody will have access to them. Regard those things as benefits of racism, then somebody would have to lose out on them when racism is taken out of the equation; it is worth noting that adherents of the notion of decent housing/careers/police treatment as privilege rarely advocate that they themselves actually lose these privileges, rather that they continue to enjoy them, whilst maintaining the additional sanctimonious high of "being aware of one's privilege". If these things are privileges and benefits of racism, then GIVE THEM BACK. Quit your job (that somebody else should have had by right), sell your possessions, burn your college qualifications, and move to an impoverished neighborhood.
Or, consider the possibly that because group A suffers from racism, it doesn't follow that Group B necessarily benefits from it; Group B would only benefit if it acquires something that it couldn't (or shouldn't) over-wise have gotten.