Migrating to Office 365 - vault suggestions
You might want to consider a third party product to help with your migration. There are several on the market, including Archive Shuttle (link in signature)
These tools will help you seamlessly migrate the archived data to Office 365.
Doing it yourself, or via a 3rd party tool/consulting, the methods are essentally the same. You have to export and then import each individual archive. Yes, it is very time consuming and requires a significant amount of time and resources to run this effectively. The alternative to migrating all this data is to use EV with O365, see following whitepaper:
there's quite a number of differences between doing it yourself via manual means and using a 3rd party tool with expert consulting to accomplish a large scale EV to O365 migration. we dont have to get into them here but i'm happy to have a conversation with you offline to help.
as for using EV with Office365, it depends what you're trying to accomplish. since you're on EV 8 with Windows 2003, the first order of business would be an overhaul upgrade of your EV environment to get you up to EV 11. When EV 11 SP1 is released (later this year hopefully) it will help round out the picture. i dont think there's any public documentation on it yet but there are some awesome new features coming out.
