First search hit for "Streets and Trips 2010" is the Microsoft web site, showing that Windows 2000 is not a supported operating system:
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Supported Operating Systems: Windows Server 2003; Windows Server 2008; Windows Vista; Windows XP
You cannot give your second install to a friend. From the EULA (emphasis mine):
Quote:
b. Portable Device. You may install another copy on a portable device for use by the single primary user of the licensed device.
Strictly speaking, this would seem to preclude even a family installing it on two computers and having two different people use them. Practically speaking, this clause is self-policed by the user. The only information that the activation server has is the total number of installs.