In the context of the two other choices presented (country & pop) which is more likely? Or does WAAF just continue as the weakest link?
I think the competition for both formats in Boston proper would be too much. WAAF has a mediocre signal in Boston proper and the immediate Boston suburbs within Route 128, and not enough people have HD radios to hear it on WWBX HD2 (Boston) and WEEI-FM HD2 (Boston and north of Boston). It's signal is best in the Metro-West suburbs beyond Route 128, and toward Central MA and its original home town Worcester.
For pop CHR in Boston, it would be foolish to go against high-rated WXKS "Kiss-108" and lesser-rated but co-owned WODS "Amp 103", though they may get some ratings in Worcester with it because Worcester doesn't have its own CHR. But, at times in history, Boston had several Top 40 stations on at once, so who knows?
For adult pop (AC), they would not go against high-rated co-owned heritage WMJX "Magic 106.7", and iHeart has AC locked up in Worcester and Central MA with longtime 96.1 WSRS.
For adult pop "Hot AC", Boston has co-owned WWBX "Mix 104.1", and Metro-West/Worcester has 104.5 WXLO (with several Boston area signal boosters).
For Country, I don't think they'd do much in Boston against Beasley's strong established 102.5 WKLB and iHeart's lesser challenger 101.7 WBWL "The Bull". They may get some Country traction in Metro-West beyond Route 128 and North Central MA against "Nash Icon" 98.9 WORC-FM Webster, MA that has a mediocre signal in Worcester and to the north.
None of those options look to me worth giving up being the only "Rock" station (not "Classic Rock", not "Alternative Rock") in the Boston/Metro-West/Worcester market (excluding NH and RI "rock" stations that are even weaker signaled in Boston), but what do I know?