Outlook and other email programs are great at handling multiple addresses. I recommend just setting up direct connections for each email address. It's easier to reply using the correct address as well.

On my phone, I have two personal addresses and one work. On my personal laptop, I have 3 personal addresses all being pulled by Outlook. It's a matter of quickly scanning down the list of Shortcuts. Each mailbox has its own set of standard folders that are sync'd with the source mail system. I have some rules that are mailbox specific. I can even have separate calendars and contact lists.

I'd hate to have to deal with all those addresses inside one inbox. Too much chance of using the wrong address for replies.