A customer recently asked me how to increase the boot disk size of a Windows VM to increase the space available to WSUS.
I recommended using the WSUSutil command to move the data to a different drive rather than extend a boot drive.
Extending drives in ESX is very straightforward and it will work on a boot drive, however, Windows will not let you extend the boot drive into the new space using diskpart, whereas it will allow it on a non-boot drive. So you normally have to use a helper VM or use something like GParted to help you out. So for simplicity and probably best practice moving the WSUS data to a new disk is preferable.
So, add a new, bigger drive to the WSUS VM (which can be done without restarting the VM) go into disk management and format it as usual. Now use the WSUSutil command line utility to migrate the data to the new drive. This link should give you some good pointers on how to use the tool.
If you find that the data migration fails due to locked files etc, then try using something like XCopy or RoboCopy to migrate the files and then run WSUSutil again with the skipcopy parameter.
Hope this helps.