I’ve come across a couple of interesting sites, mostly ones that have been linked to the American Folk Art @ Cooperstown site, that highlight folk art finds and curiosities. Candler Arts is a treasure chest of the neat and obscure as is Anonymous Works which listed this cool Carnival Wheel from the 1930’s that features cartoon characters of the time around the outer edge. There was probably a board with corresponding squares for each of the characters where a wager of some sort was made. If the spinning wheel came to rest on the Dick Tracy or Wimpy that you chose, then you would win.
This is a really interesting piece that has a pop art feel. I can name quite a few of the characters but there are a few that evade me. For those who can’t live without a piece of Carnival Americana to hang on their playroom wall, this is still available on ebay even as I write this.
Redtree Times 
I have to say I’m completely stumped by the dog (?) at about 8 o’clock.
The eBay seller says he can identify 17 (out of the 20). I’m sure your faithful followers can, collectively, do better.
I’ll take a stab at the first five (the northeast quadrant):
Olive Oyl
Jiggs (of “Bringing Up Father”)
Donald Duck
Wimpy
Fritz Katzenjammer (of “The Katzenjammer Kids”)
After doing a quick search, I think it may be Napoleon from a strip called Napoleon and Uncle Elby that ran from 1932 into the 50’s, at least. Here is a link to an issue of LIFE magazine from 1944 that has an image very much like that on the wheel. I was not aware of this strip myself.
I love folk art. If I had a spare $650 lying around, I might pop for this.
My wife, on the other hand, may not see the joy in it that I do.
I’m no help. I can only recognize twelve and identify nine. It is a great piece. If it goes for $650, I’d say the seller won that wager. 😉