For example, instead of choosing the historic plantations or sunny beaches of Virginia, Guffey chose an industrial view of a train track in Suffolk.
For his own home state, however, he acknowledged that he made an exception.
"For some reason, I came back to the simple garage scene that I'd passed by 1,000 times," he said of his Kentucky painting, the final one he completed in his state series.
Since March 2008, Guffey has painted nearly 100 images from Google Street View, in addition to more than one hundred others. In total, he said he has sold 30 to 40 pieces, some for as much as $1,500.
For the past six months, he has also encouraged artists around the world to join him with his monthly "Virtual Paintouts." At the beginning of each month, Guffey announces a location and invites participants to send him painted views of the city. At the end of the month, he posts them all on his blog.
So far, he said the paintouts have attracted about 25 painters from North America, Europe and even Australia. In the near future, he said he hopes to expand his outreach to disabled artists, encouraging them to virtually travel to and paint the places they may not be able to be reach physically.
For its part, Google has been supportive of his efforts.
"When we were creating Street View, we were excited about all the everyday uses, like looking for parking or planning trips," Stephen Chau, product manager for Google Street View, said. "Bill's use of Street View, to inspire his paintings and to create a virtual community of artists, is a remarkable example that we hadn't imagined but are really excited to see. It's been amazing to see the possibilities that have opened up as Street View has been brought to more places around the world."
But now that Guffey has traveled the country – and the world – with Google, he's itching to do it for real.
"That's one of my goals," he said. "To be able to go to the spots that I painted virtually and paint in real life."