As usual, I’m going to say that any number of potential issues can arise depending on your plugins and any customization you may have in your theme etc.
I manage a number of WP sites and I have rarely attempted to upgrade by multiple version at once without doing it one version at a time as you got to work in the end. In the cases where I have done so I noted that the sites themselves were quite small and had a very low number of plugins (plugins that I would consider to be stable and well updated).
While I don’t have an exact answer, I can say that you have already found a pretty reliable way to avoid this problem in the future by upgrading one version at a time. I would recommend this method anyway because in the event where there is a certain version that breaks functionality somewhere in your site at least going one by one will be the easiest way to get your site to the most up to date version that functions.