When: Based on the license plate on the car in the foreground, and the lack of foliage on the trees, this was taken in the late Fall or early Winter of 1940, or early in 1941.
Where: Charleston, SC. The license plate was a great clue to find the state, and it seemed Charleston was a likely candidate. A closer look at the sign at the far left reveals an entrance to the Brewton Inn, and some Google Searches reveal that indeed there was a Brewton Inn located in Charleston. Finding the specific location was interesting, and I'd actually passed over this location a time or two because the house in the background on the rear corner was not present. However, upon further review, the remaining clues are enough evidence to conclusively point to this as the spot of the photo.
Who: Only a few people at the far left, and no ID on them.
How (much): Another of the photos scored from the ebay lots which also supplied me with the Weekly Kodachrome #60, taken by the same photographer. All told, about $2 to $3 for this slide.