ITunes tells me my songs are all "Unchecked".  What does this mean?

Should I "Check" all my songs?  If so, how do I do it?  (All songs are on Windows Vista.)

That's consistent with all the tickboxes to the left of the tracks (in List view) being unchecked.
Go into List view and Ctrl-click one of the empty boxes to do a "global recheck".
If you can't see the tickboxes, head into your General preferences tab and select "Show list tickboxes" as per the following screenshot:

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