@DustinB3403 You never touch grub yourself. You let the system take care of it for you when it adds or removes kernels.
As to removing old kernels, it depends on the distribution you use. A good distro just takes care of this for you. The annoying ones make you do it manually.
RedHat/CentOS/Fedora = automatically cleans up older kernels. You don't do anything and it will keep a sane number by default. I think it's 4 and a recovery option.
Debian/Ubuntu = keeps all kernels till you manually remove them. I forget offhand what the command is besides it's an option for apt.
This is one reason I'm happily moving things from the old rental box to my new server for my home lab. The old rental box has Ubuntu with a tiny little 256MB /boot partition. It can keep ~3 kernels, and that's it, ugh!
You can install without /boot. IIRC there is a other config change with unattended-upgrades to auto remove kernels.