Your explanation is basically correct, Mike, with a few clarifications:
In most of the northeastern US and California, the most powerful FM signals allowed are called "class B" - 50,000 watts from an antenna no more than 492 feet above average terrain, with power adjusted downward from there as height goes up. In the rest of the country, where markets aren't spaced as tightly, "class C" stations are allowed - 100,000 watts at as much as 2000 feet above average terrain.
All other factors being equal, any class B station with maximum facilities will go out as far as any other class B station. For class B stations, the FCC says it's 65.1 km from the transmitter site to the "protected contour." It's certainly very possible to hear a station beyond that radius, but its reception is not protected from interference from other stations beyond that distance.
In the real world, of course, all factors are NOT equal. Terrain can affect the reach of an FM signal, as can factors such as multipath (signals reflecting off buildings, land and water) and even the choice of transmitting antenna model and the placement of the antenna on the tower.
And then there's interference from co-channel and adjacent-channel stations. In the crowded northeast, just about every FM signal is short-spaced to every other FM signal, especially since so many of them were in place before the current FM spacing rules were established in 1964. So WBEB, for instance, can't be heard as clearly to the north and east for as far as WOGL, since WBEB has to contend with co-channel interference from WCBS-FM on 101.1. (Same deal with WPST/WDAC on 94.5, WYSP/WQKX on 94.1, and plenty of other station pairs.)
Some FM stations that predate the 1964 spacing rules are allowed to continue operating at higher power levels than a normal class B station, but they are not protected from interference beyond normal class B spacing. I don't believe there are any such "grandfathered superpower FMs" in Philadelphia.
So which Philadelphia FM gets out best? It depends on direction, of course - but all of the Roxborough class Bs (94.1, 95.7, 96.5, 98.1, 98.9, 101.1, 102.1, 104.5, 105.3) are roughly comparable in transmitting facilities, with the big limitations on their reach coming from co- and adjacent-channel stations nearby. In practice, WOGL seems to me to have the clearest channel; you've got to go up to Binghamton or out to Altoona to hit the next stations on 98.1.