Like many others who are philosophically inclined, I do find paradoxes interesting. However, many seem inapplicable or impractical in real-world considerations. I believe this paradox is a bit flawed because it isolates the entirety of the obligation into a single moment. There is no mention of any future wealth you might accrue. Any pending wealth you might receive would still be held under the obligations to Tom and Bob.Suppose you borrowed $10 from Tom and $10 from Bob. On your way to repaying them you are robbed of everything but the $10 you had hidden in your shirt pocket. By no fault of your own, you now face the following paradoxical dilemma:(1) You are obligated to repay Tom and Bob.(2) If you pay Tom you cannot repay Bob.(3) If you repay Bob you cannot repay Tom.(4) You cannot honor all your obligations: in the circumstances this is impossible for you. (By (1)-(3).)(5) You are (morally) required to honor all your obligations.(6) You are not (morally) required to do something you cannot possibly do (ultra posse nemo obligatur).
Furthermore, it neglects the notion that you are (morally) required to fulfill obligations insofar as you able, i.e. as much as you can. It seems to me that you would at least be obligated to pay to Tom and Bob $5 under the simplest considerations. It may be argued that you might pay one or the other more out the $10 based on percentages of total wealth invested. However, this is beside the point. There is no reason to assume that your obligations are completely null because you cannot fully satisfy them, especially in cases involving something that is relatively easy to measure (money).
Thus, I think this paradox is, at the very least, poorly constructed. It seems to propose a problem that really isn't a problem. However, I'm sure you could add other circumstances into it to create an actual problem.
