There is always a risk that a kernel can be bad or crash or whatever. But if you do a new install, it's best to upgrade to the newest kernel available at that time, because if things go wrong, it's easy to re-install, not much lost.
So on a fresh install I would certainly recommend to update everything to the latest version (as far a supported by DA), so kernel too.
After that, normally the old kernel is kept so if things go wrong you can convert, but I know people who almost never update their kernel unless there is some dangerous vulnerability.
So it's your choice, it's not really a requirement at this moment as far as I know, I don't work with Debian. As long as things work fine and no specific kernel requirement is present for software or application on the server, there is no need for an update.
Maybe
@Zhenyapan can tell you more, he works with Debian if I'm correct.