I don’t believe all pop-ups are ugly. Unfortunately there are tons of bad pop-ups that we can point to so one can get the impression that there is no such thing as a good pop-up. There is one example I like to point to of a good rooftop addition.
Over on the 1600 block of 5th Street, NW between R and Warner there is a house with a cute rustic addition. I’ve been inside once and the owners did a wonderful job with creating a new space in their home. Maybe the key in this is that it was designed and done by the people who were intending to live in the home and not a know-nothing small time developer/contractor trying to stuff a few more square feet on to a small lot.
A few things makes this addition work. One is that it is on the end of a row of houses. You can get away with more on the end than you can in the middle. If the style changes up on the end of a bunch of uniform houses, it doesn’t break the pattern. Second, the addition, including the railing is set back from the street. Third, there isn’t a big empty space on the addition between the top of the roof and the top of the door/window. There is another pop-up on S Street, that’s lovely from the back but on the front there is this empty space that makes the front of the addition, ‘blah’.
I think the most important factor was that the addition was put on for the people who live in the house, and not some unknown buyer to be gouged of money.