Playing a 17 year old song definitely isn't a sign of a possible CHR flip. DRC knows better. You're in a market with Kiss 95.7, a CHR coming up on it's 30th anniversary, and TIC-FM, which has been CHR, Hot A/C, or adult CHR and very successful for over 36 years. There's also KC101. Hartford's all set with CHR.
I often think about the origins of the "oldies" format. The first song ever played on CBS-FM after their flip to "oldies" was Runaround Sue. The song was 11 years old. CBS-FM also played 2 currents an hour during their first decade. I think a station that returned to the original concept could have some success. 20-30 year old songs, some newer that fit the feel. In the early days, CBS-FM would play standards, which were the same age or younger as many of today's "oldies," but even those were dropped by the end of the 70's.
The idea that a "TRUE OLDIES" station can only play music from the 50's and 60's, that dropping the 50's and 60's is blasphemous, and that playing the 80's is unfathomable, is just crazy. It was never, NEVER, intended to be that way.