Do you all suggest Ascending 1 character at a time through or would you do 2 concurrently?
If I take Fortunate on a Warrior and Treasured on my hireling rogue, do I concurrently benefit from both Ascensions?
I would suggest focusing on 1 if the 2 characters aren’t always going too be the same level if they will always be the exacts same level then do 2! 
and as for the other bit the only ascension that works on your hireling is dealer hope that help 