Funny thing there is that those rules have since changed. When you're looking strictly at radio-only ownership, with no TV cross-ownership involved, it's all done by Arbitron metro now. KFI doesn't count at all anymore in San Diego, and wouldn't even count against Riverside/San Bernardino.
Yet the Puerto Rico waiver was just done this year... where the Commission essentially said that the MSA definition was not realistic.
Puerto Rico is almost the textbook example of a "special case," though, given the size of the island and the extent of the simulcasting to cover the island with San Juan-based programming. The Commission has held quite firmly to the MSA definition for radio markets in the continental US since implementing that rule.
I think it depends on how much CBS wants to upset the whole applecart.
There is a "gotcha" in the definition of MSAs that could be easily exploited. Or maybe a couple of "gotchas".
First, MSAs are dynamic. They can be redefined, and many are, annually based on the amount of listening in outlying counties to "home" stations and the percentage of commuting to and from the home county(s) by residents of the outlying counties under evaluation. Evey year brings changes in the county makeup of quite a few MSAs.
Second, in certain cases, expanding an MSA may be warranted based on the above test (the combination of listening and commuting) but not wanted
by the subscribing stations. For example, LA MSA subscribers and Riverside / San Bernardino MSA subscribers were polled by Arbitron to merge the metros, but neither group wanted it. Riverside stations would find their coverage areas and listenership diluted into oblivion. LA stations, many of which do not cover the Inland Empire well, would also see lower shares of a larger market. So the markets were not combined. Yet, 32 years ago, the separate markets of Miami and Ft Lauderdale were combined in a new MSA because the big signal FMs voted "for" and all the AMs voted "against."
So CBS could argue that MSAs are essentially fluid and often political in definition, and that a well reasoned request for a waiver, based on evidence of distance from the central city of the subject station COL, could merit consideration.
The Puerto Rico decision was based on the combined factors of distance and terrain. CBS could reference it as evidence of an exception. To ignore a decision in Puerto Rico would enhance the already existent feeling that the FCC looks at Puerto Rico with "benign neglect" and in a charged political environment CBS could argue "well, are you saying that it is OK for 'those people' but not for New York?" I'd love to read that argument!