you have a tilt shift camera and you fiddle about to get everything into the right plane on location or you don’t have one and you do it in post
either way your building is going to look very pointy on the top or your interior might have proportionally too much ceiling
You do not get the problem if you use movements... if you keep the sensor parallel to a rectangular building, it looks rectangular in the picture...
In your skyscraper shot, if the top of the building in the foreground comes opposite a point h% up the building behind (or the hth floor of a 100 floor building) that is how it will look (as a proportion of picture height, using shift to keep parallel) in the picture.
The unnatural look you get is the result of stretching the whole picture, and you (attempted to compensate) with progressive stretching.
Unfortunately, your technique makes square windows look rectangular in the upper floors.
It would be possible to correct the barrel distortion in the interior picture (bent ceiling line)... this would be a PITA, but it would increase the apparent height of the far corner of the room.
Does anyone know of any decent software to do this? Last time I tried it in PS you had to extend the picture so that the distortion was symmetrical (so that the fattest part of the barrel was in the middle of the picture) and in this case you would also have to split the picture in two.