I have seen my files being uploaded simultaneously by more than one host ... So Yes afaik this is quite possible.
I think you may find that where you saw the same host twice, that one of the files might have read "upload limit reached, or the sum of the two, if incomplete, added up to 100%. If a Limewire user tries to upload the same file twice in parrallell, he will not be able to do it. I think this applies to Phex too.
I hope this helps..
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