Given the specific questions you're asking, any court action in the US would be a civil suit brought by the copyright owner, not a criminal prosecution brought by the Dept. of Justice. This letter from the DoJ explains the policy on prosecutions and while they are non-committal on many issues, it is clear that
the statutory scheme also requires that the government prove, as an
element to any criminal violation--felony or misdemeanor--that the
infringement has occurred "willfully and for purposes of commercial
advantage or private financial gain."
Even if making thumb-drive backups is a violation of the EULA, it is not criminal infringement.
Then one must inspect whatever license terms exist for use of the content. Musical content is often vended with minimal licensing of unclear authority, but commercial software is generally vended with a license agreement that is directly presented to you and you have to at least say "I agree". A license might explicitly allow, forbid, or be silent on a particular kind of copying. Copyright protection only protects the creations of the creator A, and does not lay claim to the creations of user B who uses A's software. Therefore you can sell documents that you create with Word for large sums of money, as well as backing them up.
Whether or not you can use "peripheral stuff" created by the copyright holder, such as clip-art, depends on what the license says. Some such files are licenses for any usage, not everything is. Explicit statements of permission are very useful in that situation (also explicit denials). If you cannot find an explicit statement covering your case, there is a risk that you are violating copyright law by copying material without permission.
In general, one has or had non-statutory permission to make backups of your installed "stuff" (software, ancilliary files, music and so on). It is not safe to assume that you have permission to make duplicate copies of an installation CD (if you have one), rather, the installation CD is the backup and you execute the installed copy. It is also not guaranteed that you have permission to make backup copies on other devices, indeed there may be technical means implemented to limit you to just one installation (which can cause problems if you don't uninstall before the drive crashes). It's all in the agreement, and there is a reasonable chance that with current software, you do not have permission to make a backup copy. 17 USC 117 has a provision for "archival copies":
that such new copy or adaptation is for archival purposes only and
that all archival copies are destroyed in the event that continued
possession of the computer program should cease to be rightful
but this exception is only extended to
the owner of a copy of a computer program to make or authorize the
making of another copy or adaptation of that computer program
However, even if you paid money, you are not necessarily the owner of a copy of the program, you may be only a licensee or renter. The Regster of Coprights does not know (cannot legally determine) if you are the owner of a copy of Word 2003. This MS license agreement is explicit (except in terms of what product is so licensed), that (1) "The software is licensed, not sold" and (2) "You may make a single copy of the software for backup purposes, and may also use that backup copy to transfer the software if it was acquired as stand-alone software, as described in Section 4 below".
