I would think that Trump (being into real estate and such) would have been at least a little bit interested in owning the two tallest buildings in NYC. Not just the tallest but also the most iconic buildings! BUT since he knows about buildings (or can pay people who'd know), he would have known about the amount of asbestos in those towers, how much remediation would have cost, the difficulty of doing that remediation in that location, etc.

Hell - it may have even been a bit of an inside joke in NYC - "Buy the WTC and then blow them up for the insurance money!"