There is an "Appalachin legend" that when WSAZ Huntington WV (analog 5 1949 until it switched to 3 in 1952), first started, there were viewers in Cuba. I don't know if it was channel 5 or 3 signal.
I do know during a strip mine reclamation project on a KY - TN hill top in 1973, Channel 3 Huntington often came in better than Channel 3 Chattanooga. It just depending on rabbit position.
E-skip reception would have been entirely possible, but regular reception, I wouldn't count on it.
WSAZ did, in the early days, run very high power, and from what I've heard, was powerful enough to overtake WLWC within the city of Columbus, which shared channel 3 for about a year in the early 1950s (I refer to online accounts, I wasn't around in those days ). Not sure what the people at the FCC were smoking, to think that two low-VHF stations 100 miles apart could share a channel.
In southeastern Kentucky, a few cable systems tried to carry WHTN (now WOWK) as well as WLOS, both on channel 13. That would have required some seriously directional antennas in tandem. In that same time frame (1970s), one system in Harlan County tried to carry WCPO-9 Cincinnati, then one or two years later, another nearby system attempted WSOC Charlotte (this per
Television Factbook). My guess is that the former operator invested in an antenna cut for channel 9, couldn't provide a viable signal, and then passed it on to the other system, "hey, this antenna doesn't work for us, put it up on your tower and see if
you can get anything with it". Unless someone found the mother of all sweet spots, signals would have had to be absolute trash by the time they traveled those distances. (Or perhaps WSWP Grandview WV went on the air and compromised both stations.) WSOC actually appeared in TVFB with 5-24% viewership in Harlan County one year.
It would be nice if there were some old-timers in the industry up there from back in those days who could be interviewed and see how it all rattled out, but anyone who would know, probably isn't around anymore.