I did that before I asked, and found a Wright house 2 blocks from where I grew up (in Beverly, not Oak Park) that was a "money pit", because the previous owners had built an addition and plastered around the interior, and they decided to restore it and add period-appropriate window decorations. I didn't find any references to money pit Wright houses in Oak Park.

I'm the weirdo who actually reads our local newspapers, for what it's worth. Like I said, I actually live here.

For those of us too stupid to guess the appropriate search terms to get relevant results, would you kindly offer up some hints?

Try searching with “remodelling”, “cold winters”, etc?