I made a Cutout map of downtown Calgary using TouchDraw on the Ipad. Plus a lot more steps as well. The reason for many blocks not getting cut out was that I was experimenting with the pressure on the Cricut Expressions during the cutting session. It seemed to need maximum pressure on this particular piece of vinyl. The challenge was with the high pressure the piece was looking like it was going to shift off of the cutting mat.
Cutout/cutwork maps seem to be a trend, here's one in paper of Madrid. Mine has nowhere near the accuracy of Karen O'Leary's work however; I just wanted to see how it would look. Also the underlying map I was using did not have a lot of detail. The advantage of making an svg file is that I can make many copies. Each one will be unique due to the underlying colors of the vinyl.