With buying sex it's a bit more complicated because you have culture/religion messing up the status messages. But let's look at the margins: does a high-roller in Vegas lower his status by ordering girls to his room? I don't think so.

You're introducing too many variables to consider. Take this out of rationality, and into intuition, because that's where status evaluations are made anyways. Pause for a second and picture the person who is hiring six prostitutes.

Does he -look- high status? Is he short, or tall? Is he wearing nice well-tailored clothes, or are they alcohol-stained and rumply? Is he lean, or overweight? Is his arm over the shoulder of one or two of the prostitutes, or at their waists? Are his teeth clean and white, or plaque-colored? How obviously drunk is he?

Now picture the guy who is engaging in another form of conspicuous consumption, buying a night of drinks for a bar. What does he look like?

More importantly: What images do you think -other- people would conjure, when they imagine these two people?

Given only the information that he's rich and hired six prostitutes, most people aren't going to picture a well-groomed businessman. You leap to a lower-status class of rich - hip-hop mogul - where hiring six prostitutes might be acceptable, without apparently realizing you're shifting to a lower-status class of rich. (But even among hip-hop moguls, however, buying six women suggests you can't seduce them.) I'd leap to rock star, another form of lower-status rich.

Is it really a matter of sign-flipping, or is it just that the same status level can seem low or high depending on what you're comparing with? If a Blackberry signifies (or signified) middle-to-senior-manager status, then it's a high-status signal for a minion and a low-status signal for the big-company CEO. If inviting six hookers up to your room in Las Vegas signifies not-very-classy-high-roller status, then again it's a high-status or low-status signal depending on the starting point. Nothing needs to flip; it's the same status in either case; but the reference point (set by other characteristics of the person or situation) can be lower or higher.