Question about Outlook Express

I personally have a very strict backup policy, and at least once a week I use Microsoft RichCopy 4.0 to synchronize all new and modified files on my local hard drives to specifically categorized external devices, which themselves are locked away to prevent being stolen.

I would like to modify my backup policies to not only make use of external USB drives, but SkyDrive as well, for which I have a total of 25GB of space online. And in using SkyDrive, it is my intention to only backup the absolutely most critical information and data that I cannot afford to lose under any circumstances.

A have already setup both the Documents and Pictures Libraries in Windows to include the "Documents" and "Pictures" folders of the local synced copy of my SkyDrive, so that any files that get saved there are automatically uploaded.

Now, finally, I get to my question/s:

1.     Being a registered Windows 8 and Office 2010 user, I genuinely do not wish to lose the software. If I where to create ISO Images of my Windows and Office installation media, and upload them to a private SkyDrive folder, along with key details, would that constitute a violation of the license agreements for not only SkyDrive, but Windows and Office also?
2. If necessary, I could also upload pictures of the packaging and media to prove legitimacy of the created ISO images.
3. I could also, depending on the outcome of my queries, archive all related data files into one single password protected ZIP file (one for each product) in order to improve security and to prevent unauthorized access to said media should my SkyDrive be access by an unrelated third party.
4. Also, as a matter of convenience, will I also be allowed to consolidate and upload data from third parties (Drivers, Utilities, Codecs, etc)? Or would I as a matter of course need to get in touch with said third parties also?
   

Now, if you are curious as to exactly why I would want to do this, it's because that by my very nature, I am a very paranoid (for lack of a better word) person, and I'm afraid that should disaster strike, and the original media is lost, along with my USB Drive backups, I would suffer a setback from which I would not recover.

By uploading all my most critical personal data (which I'm already doing), along with digital copies of legitimately purchased products onto my SkyDrive, I will at least be able to restore the most valuable information and resources required to recover from disasters with relative ease, even though at worst my own primary backups are lost.

Also, a marginally off-topic question:

If I purchase additional SkyDrive storage space, does it need to be renewed on a regular basis, and if so, will payment need to be made monthly or annually?