I know that PSP has a similar feature with its Picture Tubes thing. Not sure how much size and jitter you can apply as they come out tho. My ViewingDale app has a path feature where it will do adjustable size and rotational jitter but its only done using the one brush that you have picked up not a series of them in a 'tube'. However, with mine you can go back and pick each one up and move it or adjust it if its placed really badly. Or you can delete a house or two as required. There is also the option to group a set of houses together in a line and then drop them down with the same randomized jitter too but you would get the same sequence of houses each time.
I still think some automated house position placement based on some intelligent rules is whats required. Preferably with a rip up and replace ability to progress the sensibleness of the layout. I started writing something for that but I got bogged down with it and abandoned it.