My brother bought a copy of Live 5 not to long ago, unfortunately he's now going back to school, hence he will be taking his computer with him. So my question is, if he gives me his Serial Number, which I'm 100% sure he will, would I be able to get the challenge/response code from Ableton?

I asked him and he said that as long as is okay he will do it!
Thank you!!!

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To transfer ownership of Live to you he is supposed to uninstall it from his computer. If he plans on still using it, then you would be violating the user agreement. Live's agreement allows one user to have the software on two computers(e.g. desktop + laptop). The challenge/response will work if he has only done it on one machine, but may not if he has done it on two. They reserve the right to revoke your brother's license if he violates the agreement and then the software could never be put on another computer using that serial number.

yup, all that is true... becareful, most companies are smarter than you might think