From what I can gather, the estimates were based on gross soil types in a general area, but it also appears like they did measured signals on Class I-A and Class I-B stations to determine real service areas, and Directional Antenna Proofs of Performance from the early DAs from the 1930s to 1950s, mainly for Class III-A and Class III-A stations authorized from that era. Some other areas appear to have been largely estimated without much data. Vast areas of the country only had 250 watt nondirectional Class IV stations which were only supposed to serve an area within a few miles of the transmitter.
I cannot get many people to agree to its validity, but in my state of Michigan, there is a Quaternary Geological Map which appears to correlate much better to conductivity in much smaller areas. There can be considerable variations within each County. This is why many stations have been squeezed in and have been allowed to increase facilities. Many stations in Michigan have measured conductivites and increased facilities, several to 50000 watts, but though granted CPs, few were built because of construction costs and power bills. One station was originally authorized with 2500 watts, but it gradually increased power and upgraded with extensive measured radials to 50000 watts with the same tower arrangement.