It's hard to tell how good front office are at their job, but even if you add Rychel to Sakic, Billington, MacFarland it's a lot of people who are relatively inexperienced. It would be nice with someone more experienced in the mix, even if it's not in the top role. Dubas at least had the benefit of having worked under Lamoriello and with Babcock for two years. That's a lot of winning mindset around him.
I guess MacFarland was with Blue Jackets for a while and Billington has been with Avs for a while but both teams have wandered aimlessly in a competitive sense for the last decade so it's hard to argue they have been brought up in winning environments.
In the end if you replace Sakic with a similarly inexperienced guy, it's not like you are losing a lot. I don't get the feeling Sakic loves this job, but perhaps it's the losing he dislikes.