You can make anywhere look depressing. New York is the seen as one of the greatest cities in the world, but take pictures of the right places and you would think it was Rome as the Visigoths were coming over the wall.
This. Now with a several of these unincorporated communities, and towns under 3000, they are in fact a dump where the original business building were all build in 1900 and havent had anyone occupy them for 30 years. There is no money in those communities and the outskirts of many of these have city commuters living there because the property cost is lower. These are also his bread and butter and taking pictures of these places under cloudy grey skies is artsy. His site is about old buildings and Main Street had been on a downward spiral across Iowa until about 10 years ago.
I don't think he is trying to represent Iowa poorly, just taking pictures of old buildings.
Look at the Mount Pleasant pictures. That is more like what Main Street Iowa looks like now a day (except in Keokuk apparently, yeeesh). It's the old brick "block" buildings where the top floors are often just empty/storage, but street level is full of businesses because there has been an emphasis on this in many towns. Look at Cedar Fall's Main Street as an example of what everyone else is trying to accomplish (often with far fewer resources and weaker fundraisers at the helm).