The Google problem is worse in most ways. I work for a company that contracts with a state government. Company has Google Apps for business, state has Google Apps for government, and of course I have my personal Google account. I can't use all three at the same time, unless I have a Chromium build as well as Chrome and then use Firefox or IE. I have to constantly be logging into/out of/switching accounts. I couldn't use Google talk as it doesn't work with more than one account. Hangouts isn't working yet from the government perspective, and I need a more recent build of Chromium to install it for my company. So I end up using IM+ Pro for Win 8 as at least I can be online with all three at once. This still creates weird issues as to which account is which and I lose messages and/or never receive some.
With Microsoft, I have one main personal/developer MS account that is both Xbox Live/Windows Phone/etc. I also currently have one non-profit Office 365 account, with another on the way, and a school Office 365 account as well. The insanity wrapped around this isn't bad yet, as I don't use the school or secondary O365 account on a regular basis.