I think intuitively it's easy to think that going in steps is somehow more cautious. However, with the exceptions of versions you cannot skip past, you are running all the same upgrade code in newer versions. Furthermore, if bugs were found and fixed in the upgrade code they are more likely to be included in the latest version.
If you find problems then you find problems. You will still have to fix them regardless of the target upgrade version. This is why it's a very good idea to clone and run and test.