Set 'From' address in Outlook on a per-message basis

I'm trying to determine if it's possible in Outlook(2010 specifically) to select the from address on a per-message basis if the user has multiple valid SMTP addresses on their Exchange mailbox. This is one of those things that is apparently un-googleable. For bonus points, it would be awesome if you could set the default from address per-contact.

Solution 1:

In the message window, switch to the Options tab, then enable "From". This will add a "From" input above the "To" line. You can put any mailbox for which you have Send As permission.

(Picture is from this guide)

Solution 2:

In the web interface...

• Start a new email
• Click three dots menu and select 'Show From'
• Right-click your name, select 'remove'
• Type in the distribution group address you have rights to send as

It will then be a selection in the From drop down going forward.