First, the disclaimer: Bob Savage is a friend, and I've known him and WYSL since before the station was even on the air.
I live in Rochester (actually, about a mile outside the city line, in the southeastern suburb of Brighton), and whatever issues WYSL might have, ground conductivity here isn't one of them. Even as a 500-watt ND daytimer on 1030, the original configuration, WYSL put a respectable, if far from barn-burning, signal over most of greater Rochester. I have tapes of the station's first day on the air in 1987, recorded here in Brighton, to prove it.
Subsequent daytime increases to 1000 watts on 1030, then to 2500 watts on 1040, then to today's 20 kW (13 kW critical hours) gave WYSL an excellent signal over the metro. Bob's been out with his FIM and measured better than 5 mV/m at the Lake Ontario shoreline. In driving around town, I think it may be even better than that most days.
The issue, of course, is at night. Back in the 1030 days, Bob might as well have signed off during critical hours as far as Rochester and Monroe County were concerned - there's simply so much skywave from WBZ here, even before it's completely dark out, that his kilowatt was being smothered by WBZ's 50.
Moving to 1040 helped that immensely. We're well outside not only WHO's predicted 0.5 mV/m skywave contour here, but also its real-life 0.5 most nights. Even with only 500 watts at night, WYSL was very easily listenable (at least here in southern Monroe County) just about every night. That changed, dramatically, the first night WBZ's IBOC was on.
So why doesn't Bob pack up his Nautel and move north? I can't speak for him, but there are certainly some obvious factors. WYSL is the only signal licensed to Avon, so he can't move very far without taking away Avon's "sole local service," which he wouldn't be allowed to do. Then there's the question of available land: going north from Avon to Rochester, one passes through fairly expensive (and NIMBY-infested) exurbia in the town of Rush and the southern portion of Henrietta, then very quickly into the even more expensive commercial strip of northern Henrietta. Replicating Bob's widely-spaced four-tower array anywhere much to the north of his present site would cost more than the station is worth, most likely.
Oh, and as for the "station more suited for carrying Avon HS football"? While it wasn't the case even a generation ago (I remember it being a long-distance call from Rochester to WYSL when it first signed on), northern Livingston County has really become a bedroom community of Rochester these days. It's only a 15-minute drive from Avon to many workplaces in southern Monroe County, and most people in Avon (and even in towns to the south, such as Geneseo and Livonia) do the vast majority of their shopping in Henrietta. There's just not enough of a local business base in northern Livingston these days to support a hometown radio station, much as I (and Bob, I'm guessing) might wish otherwise.