One thing, i have heard that some operators will "massage" the figures slightly either through lack of knowledge, or because they know the owner of the car just wants to see big numbers.
'Funny' you mention this. There's a goose around these parts who always seem to get between 10 to 20 HPs more on his Dyno than anyone else.
As a guy from Mini Spares said to me not long ago, "Yes, his legend is well known over here, he gets 50% more on his Dyno that anyone else can"
I think it's important that the corrections are applied for the day, as they will vary with weather and other factors. It certainly gets hard to get repeatable results on a rolling road, but far from impossible, just a few more checks to be done.
A few ways of looking at this and where best to measure. The Flywheel while in the chain, isn't what drives the car, the tyres do, so anything that's measured before these only shows part of the story, though measuring at the Flywheel is easier (the lazy way) to get repeatable results - of the engine.