As for your wheel's provenience, I would assume it came from one of the underground gambling clubs in prohibition-era Omaha. Apparently they were quite the open secret. Check out
this blog about a guy trying to find the speak-easy his grandma used to frequent. Of particular interest is this:
Quote:
I uncovered a fascinating article from the OWH, dated May of 1935. There had been a recent Clover Leaf Club gambling raid where seven men were arrested. Three men were held for trail: Ike Levinson, George “Dutch” Volker and Fred Sellers, all living at the Loyal Hotel. Five other men were dismissed for playing a game of chance with two others being fined $5 each. Apparently the raid followed after two patrons turned in the Clover Leaf for offering games of chance. The officers who conducted the raid reported, “When they entered, Volker ordered Sellers to press a signal light which warned players in the rear room. Levinson denied it was a signal light, saying it was meant to summon the porter. The back room was not for gambling but a dressing room for musicians, he said.” Levinson denied there had ever been gambling in the Clover Leaf Club. The proprietors were listed as Ike Levinson, Dutch Volker and one Charles Hutter.
The Clover Leaf closed in 1939 and sold off all their equipment. It's possible that the wheel came from there, but given how many illicit gambling sites Omaha apparently had (not to mention the chance that it came from out of town), it doesn't seem probable.
Chances of finding a picture from your wheel's heyday seem slim. For obvious reasons, photography was not common in illegal clubs. Here's one taken with a hidden camera in a club near Chicago, which was the only "in-use" roulette pic I could find from that era other than in Vegas. It's not the deluxe wheel, though.