Isn't this the same joint that has a BJT with first place being a Harley motorcycle? I'm afraid that I wouldn't be interested in any BJT like this, even if it was in my own backyard - but not entirely for the reasons noted here so far.
Casinos have a bad habit of overstating the value of merchandise prizes rather steeply when they "W2G" or "1099" the winner, principally because they get a fatter tax write-off. There was a notorious case some years back - I don't remember the casino or the date - that had a new car available to the lucky winner of a low-denom bank of slot machines. That car sat there for at least a couple of years before someone finally picked it off. The casino issued a tax form for the sticker price of the car, and the winner squealed because it was absolutely not a new car any more. The whole thing ended up in court and the casino lost.
In this case, it's easily possible that HoChunk picked up the Aspen trip cheap through a discounter or similar. Let's say they paid $3,000 for it. They can look through full retail vacation pricing websites and find someplace which will sell the same trip for $6,000. They pay $3K, they issue the winner a tax form for $6K (plus the cash bonus). Perhaps that isn't what is happening here but a casino will rarely miss a trick like that if the opportunity is present.