I know I am bringing this thread back from the dead, but there are some good comments here. If I may.
The HP calculators use an algorithm to compute HP with trap speed, which is the best way to determine HP displayed on the track. It does not account for track conditions or vehicle type. It also does not account for the actual performance of the vehicle as determined by the driver's action.
A dyno is used to measure the power at the wheels. For a true dyno to calculator comparison, you need to first start with a dyno run the same day, and use the uncorrected numbers.
I use them both as tools. When I took my truck to the track, I knew the HP so I knew what the calculator said it was capable of. (or close to it). As long as I had an accurate weight, didn't have tremendous head/tail winds, and I drove the truck correctly, mine was dead on to the dyno numbers.
The biggest advantage for me using the two tools together was no matter what the dyno number was, and no matter what the trap speed, if I wanted to go faster, I needed to make more power. I could verify this on the dyno before I went to the track, and know what to expect at the track when I got there.
But I never forget that calculator doesn't know what vehicle I am driving. If it says 500hp will take a 7000 pound vehicle to xxx mph in the quarter mile, wouldn't it matter what type of vehicle it was? Wouldn't you expect a truck that is lifted will have a higher coefficient of drag (cd) over a lower 2wd at the same weight? Wouldn't the higher cd result in taking more HP to achieve that speed? Wouldn't it be effected by wind conditions more severely? Where do calculators account for this?
All things we should consider while we try to make sense of the numbers we get or calculate.