Spencer, I like your use of the sideways 1x1 and 1x2 trans black tiles to crate the Modern glass box look of the Trump World Tower.
Ersh: Glad to see you are still building. Is your Sears/Willis Tower taller than Spencer's micro scale version because you have more floors? It looks like you both used 2 plates per floor?
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By the current definition of a skyscraper used on SSP (500 feet or higher, consisting of habitable floors, etc), I have only built one LEGO model of a skyscraper, the Penobscot!
Of course shorter buildings were called skyscrapers in the past. My newest LEGO building was never really a skyscraper but considering that the prototype was completed in 1893 when the number of 10+ story buildings in Detroit could be counted on one hand, the old Union Depot on Fort Street was a tall structure for the time.
Here it is at the Great Train Expo of 2009 in Novi, Michigan: