:GetPropertyChangedValue not firing for updated values, only for the first ever value of a variable

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Would this not fix your issue? If you connect the changed event to each selection when initialised?

local currentlySelect = workspace['PLUGINPart_DoNotRemove_1a2b3c4de5f6']

local function getObject(gui)
	local obj = Selection:Get()[1]
	if obj == nil or not obj:IsA('Part') then
		return
	end
	
	GetSize(obj, gui)
	currentlySelect = obj
	return obj
end


local gui = script.Parent.ScreenGui
gui.Parent = game.CoreGui
gui.TextLabel.Text = 'TEST'

Selection.SelectionChanged:Connect(function()
	currentlySelect = getObject(gui)
	currentlySelect:GetPropertyChangedSignal('Size'):Connect(function()
		GetSize(currentlySelect, gui)
	end)
end)
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