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Cheating by using Rasterize labels = {"Long property name A", "Extremely long Property name B"}; Grid[Partition[ Riffle[Join[{Null}, Item[Rasterize[Item[Rotate[#, -90 Degree]]], Alignment -> Bottom] & /@ labels, Item[#, ItemSize -> 4] & /@ {1, 3000, 5, 7000}], Item[#, Alignment -> Right] & /@ labels, {4, -1, 3}], ...


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