Unpredictable Creation?

I created some buildings and row houses but the results are sometimes unpredicatble. By this I mean that the number of items created and where they show up is unknown before hand. Is there a rule about the size and type of multiple item creation process that might suggest a way to control the multiple item process?

A particular item is the longest rectangle that should only cover the building under it but now crosses the freeway.
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You've got me stumped on what you're asking for here. When I use the multi-house tool, it's really only for a long row of houses along a line or freehand shape. What you're picturing here I would've chosen the single angled house tool instead. The multi tool is for repetitive patterns in houses where each house is basically the same size and alignment. It was never designed for what it appears you're trying to do in that image. Maybe I'm missing something here. As a general rule I only use the multi tools if I want to draw 4 or more houses of the same size in a row.