Upgrade advice needed

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Outlook version
Outlook 2019 for Mac
Email Account
Outlook.com (as MS Exchange)
I am running Windows 7 Ultimate and Outlook 2010. My time frame for Windows 8 is within the next 6 months, although I already have it on a different drive. I have 7 email accounts, 1 cloud for calendar and contacts interface with a windows phone (soon to be an iphone), 1 MSN through the connector, 1 gmail for business, and 1 that's on Office 365 web for my second job, and 1 through my ISP <Verizon>. I pop into most. I also have 2 others on windows live mail, but I'm not sure why I did that. Can I get recommendations for transitioning to Windows 8? Thank you.
Will you keep the same version of Outlook?

Transitioning won't be difficult - if you leave mail on the pop servers you'll download duplicates when you set up the new accounts on windows 8. Basically, set up the accounts in windows 8, point the pop accounts to the pst files you use now and let the other accounts recreate the data files and sync.

The steps at http://www.slipstick.com/outlook/config/moving-outlook-to-a-new-computer/ apply to all versions of outlook and windows (dialogs might vary though)
Since it's 6 months away, I will consider the next version of Outlook. It just seems like I am fighting the cloud, and maybe that's old thinking. :)
fighting the cloud seems to be a losing proposition. :) You don't need to use the cloud features, although I kinda like being able to save directly to skydrive. Dropbox has saved my backside a couple of times so I'm liking the cloud. We use a private cloud at work so I'm used to remote storage anyway.
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