I just thought of that question a moment ago. It does seem to have a lot of potential. Machiavelli is infamous for his amoral teachings on how to build and maintain a powerful state, but I'm not convinced that such harsh judgements are justified. Yes, Machiavelli advocated expedient use of cruelty, dishonesty and other such vices, but consider his reasoning:
"Since men [other princes] are a contemptible lot and will not keep their promises to you, you likewise need not keep yours to them". Very much the style of reasoning Hobbes describes as rational, within the fickle State of Nature (as he envisaged it - rather more pessimistically than Locke!). You cannot trust others to treat you well, so there's no reason for you to be nice either - such naivety would merely serve to open yourself up to exploitation.
But note also Machiavelli's disclaimer which immediately follows: "if men were good, this rule would not be good". So it is not that Machiavelli is immoral, or even voluntarily amoral. Rather, he recognises that people within the Hobbesian State of Nature (as were Renaissance princes with regard to each other) have no real choice; they are forced by rationality into acting amorally, for it is the only route to self-preservation.
Our private lives are different though. We can reasonably expect our friends and family to keep our trust, and so we ought to keep theirs in return. Machiavelli would not contest this at all. However, I do think Machiavelli is too pessimistic about inter-principality (or international) relations, for he seems to just accept this state of mutual distrust, this "State of Nature", as being inevitable and immutable. So from that position, he (reasonably enough) offers his advice on how to survive in it.
A more interesting subject matter, I believe, would be to ask how princes could break out of their macro-version of Hobbes' SoN. At the micro level, Hobbes answer is the "Social Contract" (binding individuals into a state). Is there any reason why this very same solution could not apply at the macro level (binding states into a super-state)? Could not the princes join together in a common community, giving up their rights to a sovereign body, to the benefit and security of all?
An interesting question, I think. Translated to a modern setting, we could perhaps interpret the United Nations as attempting to play such a role (though of course it is as yet nowhere near powerful enough to enforce its decrees upon rogue states).
I wonder what Machiavelli would make of it all? Would he be a multi-lateralist after all - if only it were a viable choice? This certain seems at odds with the common perception of him. Nevertheless, I think it is a very real possibility.
Update: For all the Googlers out there wanting to know where Machiavelli (literally) lived, the answer is Florence.