was hoping to get some remastered versions of the songs without actually having to pay full price for all of them.
That's a separate issue from getting everything to either match or upload. if you have something that has been remastered, experiences to date suggest you'll have poor luck getting matches to them, simply because theyre not the same track. For one thing, it's generally believed the matching process involves waveform comparision. for another, iTunes matches based on what is "currently for sale in the iTunes store." If what you have is there, it may match (it won't always), but if it is not, but a remaster is, that's considered a different album entirely.