Why doesn't the folder update after destroying instances within it?

I'm creating a game in which you can spawn a sled which is then assigned to you. This way, you are only allowed to spawn one at a time. In order to help if you lose your sled, I've also added a gui in which the player can delete their sled so they can respawn a new one. However, when the sled is deleted through the gui, the player is unable to spawn another one. I'm not quite sure why this is the case, here's the code.

in the gui to delete the sled

local player = script.Parent.Parent.Parent.Parent

script.Parent.MouseButton1Click:Connect(function()
local descendants = workspace.sleds:GetDescendants() --this is probably unnecessary but it works
    for i, descendant in pairs(descendants) do
        if descendant:IsA("StringValue") then
            if descendant.Value == player.Name then
                descendant.Parent:Destroy()
            end
        end
    end
end)

and in the clickable regen buttons

local sled = game.ServerStorage:WaitForChild("sled_of_doom") --sled gets cloned to spawn

script.Parent.MouseClick:Connect(function(player) 
    game.Players:GetPlayerFromCharacter(player)
    local descendants = workspace.sleds:GetDescendants() --look through all existing sleds
        for i,v in pairs (descendants) do
            if v:IsA("StringValue") then
                if v.Value == player.Name then --if sled exists under players name already, do not spawn one
                    return
                end
            end
        end

    local newsled = sled:Clone()
    newsled.Parent = workspace.sleds
    newsled.PrimaryPart = newsled:WaitForChild("eee")
    newsled:SetPrimaryPartCFrame(CFrame.new(script.Parent.Parent.Position.X, script.Parent.Parent.Position.Y + 5, script.Parent.Parent.Position.Z - 10))

    local owner = newsled.owner
    owner.Value = player.Name

    script.Parent.Parent.Color = Color3.new(26,27,28)
    wait (15)
    script.Parent.Parent.Color = Color3.new(123,0,123)

end)

I'm sure the answer is probably pretty simple but I can't seem to find it right now.