You’re on to something but I doubt it’s the syllables. Rather it seems about phonetic ambiguity.
“twentynine” could mean both 29 and 2009, so it’s better to use “twothousandandnine” for the latter. “twentyten” cannot be interpreted as 30, only as 2010.
Sure, for many things there’s a deluxe version (clothing, cars, food, housing) but they tend to be physical. Since media is largely digital these days and has fantastic marginal distribution costs the rich consume the same stuff when it comes to popular media. Ie there isn’t an alternate Hollywood studio just for the rich, itunes doesn’t have a separate server, the new york times website is the same for all, etc.