Forwarding update messages

That is not a native feature within WF yet, though it would be nice. We have a Note report that can be run by anyone and filtered to the person they want to watch, but that's manual at best. 

After that, your next option is Fusion. I have a module that reviews who is tagged on Update messages, bounces that off of Delegation records, and then auto-responds with the OOO message/dates and tags in their Delegatee.

You can use the delegation functionality in WF to have tasks reassigned to X person, but the kicker is it's only a 1:1, you can't specify for X tasks to go to one person and Y tasks to go to another.

Something else our users do is add the OOO dates to their name in their profile, so anytime someone goes to tag them in an update, it's right there with their name. Like 'Madalyn Destafney OOO 7.04-7.20'.

We have OOO feature build out in Fusion which basically works like in Outlook, you can turn it on/off whenever you want or specify hours when OOO should be sent. It also takes into consideration user's time off configured in the system.

Outlook integration would be better 🙂 but Adobe killed one rather than improving it

Not to state the obvious … but you could also play with the Outlook rules to see if you can configure them to forward the message or autoreply to workfront comments.