It sounds like this logic requires a trip to a Hilton casino? Or am I missing something here?

Taking this example one step further: Turn the 110K into $400 in chips, find a white-hot dice table, turn $400 into $5000, use the $5000 to buy a whole buncha plane tickets.

Seriously though, I tend to look at double point conversions as a last-resort thing. And when I do a point conversion, I keep it as small as possible - just enough to liberate the orphaned points in question. Don't know why anyone would hate 50,000 Skymiles...if you hate DL, there are certainly lots of other awards to pick that will offer better value. Heck, if you are dying to get out of Skymiles, just stop after the HHonors transfer and go spend a free week in a Hawaiian Hilton.