It's one of the things that ground Yahoo to a halt. We spent years migrating from RHEL-4 to 6, then RHEL-6 to RHEL-7, and by the time the projects were pretty much complete, the next sunset was approaching. My cynicism comes from seeing the bad things that "Enterprise Linux" enabled there.

Admittedly, Yahoo was an extreme case. It never solved the really building problem - the culture from the early days was to compile, ship and forget. Once a RHEL-6 package was pushed to our dist/yinst system (packages), it would never be rebuilt unless it was 1) necessary, or 2) It was time to try and figure out how to build it on RHEL-7.

A lot of effort was spent in the later years to try and address this (by burning the old tech stack to the ground), but the culture was pervasive for the longest time. If 10-year-RHEL didn't exist we would have been forced to address the building processes.

If it's hard or error prone, then do it frequently until you get the process nailed down.