Now after 45k miles, my speedo is off about 5 mph above about 50, but when my tires were new (4 years ago), I entered 36.85" into the appropriate spot on my AEV ProCal chart and my speedo at that time was spot on, as measured by GPS. I still don't see how even the compressed value of the tire would be twice the measurement from the ground to the center of the wheel. The tire, rolling or otherwise, will never be compressed on the top of the tread. So the distance from tne cener of the wheel to the top of the tread seems like it would be a more constant measurement, as so many things can affect how much the bottom of the tread is compressed. Heat and ambient temperature, weight transfer under acceleration/braking, road surface (hard vs. soft), fuel....and that's not even accounting for the driver, passengers, payload, etc. The distance from the center of the wheel to the top of the tire; however, will never change aside from tire pressure affected by temperature.
I have never seen a speedo get off 5 mph just because the tires had 45,000 miles on them. I have however seen a speedo be off about 5 mph because it was calibrated by measuring to the top of the tread like you had done. Fact of the matter is, your speed sensors are only interested in the RADIUS of your tire, the point from the center of your wheel to the ground and NOT the diameter. The only reason why you need to know the diameter is because that's what your programmer wants to know. As far as gauging your actual speed goes, try using a radar speed trap or a friend following you on the highway who has a car with a known accurate speedo as opposed to a GPS.
And Eddie....just to clarify, you said in your post that people in the know refer to "advertised size", which is always smaller and I think you actually meant "actual size" is always smaller. :beer:
Advertised size as in what is written on the sidewall. In other words, if the tire says 35x12.50. Yes, the "actual" size of this would be closer to 33" tall and that would be the same as a 305 or maybe even a 285 metric depending on the make.