skilltree.vip

"Modified skill points per level based on permissions [must be higher than default]": {
      "points.vip": 10
    },
    "Maximum points a player can spend [default]": 0,
    "Modified max skill points based on permissions [must be higher than default]": {
      "vip": 10,
      "nolimit": 0
Why does upgrading to 10 skill points and upgrading to a maximum of 10 skill points not take effect after granting the group skilltree-vip permission?

Because this "Maximum points a player can spend [default]": 0,

If the default max points is 0, the perms arent even taken into account because all players have no maximum amount.

Oh sorry I didn't realize what you are saying.

Does it update on a plugin reload?
When a player's data is instantiated, it will calculate what their skill points should be at, and what they are currently at and will add the difference if its less. If they obtained skill points from external sources, it will consider them as part of the difference.