Upgrades on MR question
 

Do you try to book upgradable fares when booking MRs to use upgrade certs?

Correct me if I'm wrong, but it seems to me that when doing a MR, your first priority is to get what you need, MILES, PQM, Segments, MQM, etc that is needed to qualify for a particular TIER. Upgrades will be more of a secondary nature, however, all things considered, yes, of course.

I assume you are talking W fares (or above) on UA. I do have a friend who will book a W on one leg if he is sure the UG will clear instantly to make sure he gets a little more sleep.

Typically though, no because it kills the price.

Yes, W or above mainly for the sleep but also to use the upgrades before they expire.