Doing incremental updates is definitively more work, but it spreads out the risk of the change. It is easier to solve a few problems at a time, than all problems at once.
I would first try a big-bang upgrade of everything at once. Maybe you're in luck, and only a few details have to be fixed! But there's a good chance it will be more than that.
So time-box that experiment. If it takes longer than expected, start over and go the incremental route. Note that the time you spent on the big-bang approach will not be entirely wasted, as you will re-encounter the same problems (but now you have a better idea on how to solve them).
In the future, you can avoid this technical debt by trying to stay on top of updates. This doesn't mean you have update everything immediately when there's a new version. But you should be in a situation where you can update everything within a day or so if a security patch is released.