Sure, moving KSON to 103.7 will help North County coverage a bit, but it also carries big risks. KSON has long had strong ratings, its carried the same format for 50+ years, and even hit #1 in the 12+ a few years ago. Not smart to mess with the dial position. As for the signal issue, 101.5 KGB's tower is near KSON's, and they're both 50kw, but KGB has never had a North County repeater. They still get solid ratings.
I was once in TV management, and worked at several stations that changed networks. Even after massive ad campaigns (Fox is now on Ch. 13!! ABC is now on 11!!), inevitably the stations that kept the same channel position gained share from the stations that changed.
Kent pointed out the same thing to me when I shared an idea from a video I saw on YouTube regarding Entercom's impact in Dallas-Fort Worth. One of the ideas I shared was that Entercom should swap frequencies with AMP 103.7 and 100.3 Jack FM, meaning that AMP would move to 100.3, and Jack moving up to 103.7. However, Kent told me frequency swaps cost money to promote and they result in some confusion that would take time for listeners to adjust to the new frequencies for those particular radio stations, and said that 100.3 and 103.7's coverage are pretty much identical, stating that there's no reason for Entercom to swap frequencies for those stations. Energy 103.7 is the lowest rated CHR in the San Diego market, but has a strong signal. Therefore, I thought that KSON would have the potential to perform better on 103.7 since Entercom is spinning 92.1, and Energy would move down to 97.3.