Want to find out how much it matters? Use a broad spectrum of experienced listeners -- audiophiles, studio pros, audio engineering students with fresh, trained young ears. Use a broad variety of systems from studio monitoring systems to audiophile-approved high end. Run a lot of trials. If, in the end, very few people from any group listening to any system could differentiate any of the files (not just the up-sampled ones that shouldn't have been in the test) from each other, you've learned that it doesn't matter much.