This is a good point. The distance between versions can matter, but it usually matters a lot less than the eng/ops processes and culture of the specific organization.

For my part, every time I have done a major OS distribution upgrade, 75% of my time was spent fixing all of the things that were deployed into a highly fragile state to begin with, 25% direct upgrade-related issues (dependencies, config, behavior changes), and 5% actually performing the upgrade.