In my very small office I have had Office 365, home edition, installed on one computer (a Dell laptop running Windows 8.0). Our other computer was a desktop running Windows XP and Office 2007. We are now (late, I know) retiring the XP machine and have just set up a Dell XPS 8700 to replace it. The XPS came with Windows 7 Professional installed, with a free upgrade to Windows 8.1 Professional. It was from the outset our intention to upgrade to Windows 8.1 Pro before installing any software, etc.
We first installed all the Windows updates in Windows 7 Pro. That was probably unnecessary because the 8.1 upgrade apparently deletes all the Windows 7 hard disk partitions anyway,before setting up its own. It took three rounds to install all the updates. Then we proceeded to the Windows 8.1 upgrade. It wasn't completely obvious how to do that (it turned out that is done using the Windows 8.1 recovery disk supplied with the computer). My secretary who was handling the computer setup called Dell support and got a very helpful tech who walked her through the whole process, and also assisted with re-installing the antivirus (McAfee, came with the computer but had been disabled by the upgrade). This was a VERY positive support experience, quite unlike the disastrous one I had from Dell Support some months ago when I tried to run the 8.1 upgrade on my 8.0 laptops. Maybe somebody read the scathing account of that fiasco I posted in the Windows 8 forum at the time?
So at this point we have the new computer running Windows 8.1 Professional and have installed all the Microsoft updates pertaining thereto. We have also without incident moved our QuickBooks and Quikwater software and databases (we are a very small local government agency providing domestic water to a very small town) over to the new computer. Time to install MS Office 365, for which our license covers 5 computers and 5 tablets. There's where the fun began.
I originally installed Office 365 on the Win 8.0 laptop, in March 2014, setting up a Microsoft account for the purpose, and using our then valid E-mail address. Office 365 won't run in XP so we left the desktop alone at that time. By the time the annual renewal came around (March 2015) we had long since (August 2014) ditched that ISP (Hughes.net) and set up our own local high speed connection (Comcast fiber-optic plus direct microwave link) and our own domain, etc. Also I had managed to forget the names of the MS accounts and their passwords. I spent a couple of hours trying to get MS support, but to do that in the normal way you must first log in to an MS account, and of course I couldn't do that without account name and password. Finally I called the telephone hotline and after a few false starts got connected with somebody in the MS Office accounts section.
She was able to identify the account using the number of the credit card I used to pay for Office 365. After some convolutions to identify myself I was able to set a new password and open the account. That account was, however,still linked to the old and no longer valid E-mail address, and for the longest time (over an hour) I couldn't convince the lady that mail sent there would not reach us. She was adamant, the automatic renewal had gone through, therefore the mail account must be working. Probably so long since cancellation that Hughes no longer bothered to send an "undeliverable mail" notice. Finally I made it clear I wanted to link the current, valid E-mail address to the Office 365 account. She said that was impossible because there was already a Microsoft account linked to the new mailing address. OK, I asked, can't we just switch the Office 365 subscription to the new valid account? No,that is impossible. I had trouble understanding that because, obviously, I own both Microsoft accounts. We went back and forth for quite a while. The compromise we finally reached was that MS will allow the current Office 365 subscription to expire on its next renewal date (in March 2016) and at that time we can "re-purchase" Office 365 and link it with the MS account bearing the valid current mail address. In the meantime, in order to set up Office 365 on the new machine we have to log into the old MS account bearing the no longer valid E-mail address.-
I still think that is unsatisfactory and likely to cause problems, but after three-plus hours on the phone I decided to settle for what I could get. I just hope they haven't jacked up the price by that time.