Why does the Regen function not call after the first loop?

I'm trying to find a way to regenerate a tycoon after the previous owner leaves by checking the owner's name (stored in a StringValue) against the playerlist. The first use of the function works perfectly, resetting the tycoon and clearing the StringValue but on the second loop the Regen function is not called.

Any reasons why this is happening and how to fix??

wait(1)
local model = game.ReplicatedStorage:FindFirstChild("Tycoon1")
local floor = script.Parent
local backup = model:Clone()
backup.PrimaryPart = backup.Baseplate
wait(0.1)
backup:SetPrimaryPartCFrame(CFrame.new(floor.Position))
backup.Parent = game.Workspace

local PlayerName = backup.Main.Owner -- StringValue location

local function Regen()
	print("Regeneration Called") -- Does not call on second iteration
    backup:Destroy()
	wait(0.1)
	backup = model:Clone()
	backup.Parent = game.Workspace
	backup.PrimaryPart = backup:FindFirstChild("Baseplate")
	backup:SetPrimaryPartCFrame(CFrame.new(floor.Position))
end

game.Players.PlayerRemoving:Connect(function(Player)
	print(Player.Name .. " has left the game.")
    if Player.Name == PlayerName.Value then
        Regen()
    end
end)