visual: Jordan rips off the buttons in Danny's shirt in a pretend sexual act...
Dr. Jordan Cavannaugh: What about that girl with the impressive cleavage, isn't she gonna be jealous?
Danny: This is Vegas. You're gonna have to be more specific..
visual: Woody is loosing alot at the Black Jack table
Samantha: Woody, if you don't stop gambling, I'm gonna break your legs.
Det. Woody Hoyt: You people still do that here?
Samantha: The casino doesn't, but I still enjoy it...
So accept the premise that Woody won a $100,00 car, lost it again, and somehow will still have to pay taxes on it. He made the statement that he will have to work for two months to earn enough to pay taxes on the car. Come on, he's a civil servant in Boston, he can earn enough to pay taxes on $100,000 of extra income in two months? Certainly not unless he's on the take.
One simply can not win a $100,000 car with a single $5 bet on a Las Vegas wheel. The Wheel is not like a slot machine, it has to stop on one of the positions. Even if a wheel had 100 positions, it could not pay out such a big prize on shuch relatively short odds.
The win of the car was clearly an intentional setup by the staff who felt sorry for the guy. Also, some regular joe who know nothing about taxes will always make the mistake of underestimating tax consequences of such a huge prize. It's just a reflection on reality, not a goof.