Probably. Did you buy the stuff on your hard-drive, or was this stuff you have ripped from your own CDs?
If they are purchased MP3s from enywhere but the iTunes music store (iTMS) then they will have digital rights management (DRM) that won't work with iPods. But if they are regular MP3s then iTunes will put them onto your iPod with no problem (some people have had issues, but it is rare).
(and yes, you CAN boot off USB if your motherboard/bios supports it)
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"The problem with any ideology is that it gives the answer before you look at the evidence."
—Bill Clinton
"The greatest obstacle to discovery is not ignorance--it is the illusion of knowledge."
—Daniel J. Boorstin, historian, former Librarian of Congress
"But the Senator, while insisting he was not intoxicated, could not explain his nudity"
—WKRP in Cincinatti
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