The output wattage thing is this an art as much as science; maybe voodoo.
No, it is science and math. Until you start looking at the claimed power output of many transistor amps of the 80's, and/or some power ratings of output transformers. Then it can be pure B.S. and marketing.
It all depends on how exact you want/need to be. I like PRR's method in most cases. What the data sheet says is generally right if you have all the same conditions. If you have some different conditions, you can figure how that might change things and by how much.
Psychonoodler's method also works, but I still like PRR's amendment to that method, using a fudge factor to correct for real-life, since the simple formula will over-predict the power output. Psycho's method would work for a perfect tube and perfect power supply, but needs some adjustment for the fact that neither is perfect.
Or you do it the scientific way:
You need to put a signal into an amp. The standard frequency is 1k, which is not all that helpful for guitar, and less helpful for bass; so some people use 400k or 330k for guitar.
1k is a standard test-tone, but 400Hz, not 400k, would be a common tone for audio amps. Low E is about 80Hz. That makes the high E about 320Hz, high E at 12th fret about 640Hz, and high E harmonic at 5th fret about 1280Hz.
I've seen some breakdowns of fundamental pitches by instrument claiming that there are few if any instruments with a fundamental pitch over 1k. So 1k would be pretty useless as a real-world guage for guitar, in my opinion. Harmonics are likely present up to the limit of speaker reproduction, especially with distorted guitars. But for clean sounds, harmonics are very much lower in output level than fundamental pitches, and serve to give your ear a clue as to what instrument is making the sound.
Some people feed the signal in @ 200mV; but I think the industry standard is 500mV; some some humbuckers can put out +/- 1 volt.
There is no standard, which is how people play games with numbers and power ratings.
If you decide to measure, what do you want to measure? My view is you don't give a damn about the preamp, just what power the output section can make. So the ideal approach seems to be to feed a signal into the phase inverter, or a push-pull signal into the output tubes directly, which drives them close to having 0v on the grid. This usually pushes them to full output power at some level of distortion.
If you want precision, you should specify the amount of distortion, to give your measurements meaning in relation from one amp/measurement to another. You could guesstimate by ear, but odd harmonic distortion is more noticeable/obtrusive at a lower level than even harmonic distortion, which might lead you to guess unequally between 2 different amps. You could eyeball the amount of distortion with an oscilloscope, or measure it conclusively with a wave analyzer, distortion analyzer, spectrum analyzer, or with careful use of the scope.
Measuring the output voltage at the speaker lends itself to using a simple formula: V2 / R. But using an inductive load like a speaker gives you a moving target, because its impedance is non-constant, and has to be measured/calculated at a given frequency. So the easiest thing to do is use a fixed resistor as your load. Especially since listening to full power sine waves will make you lose your mind (let me tell you about aligning multitrack tape machines sometime...).
You have to know the amount of distortion present when measuring voltage, because the calculated RMS power of a sine wave is 1/2 the peak power, where the RMS power of a square wave is equal to the peak power. A sine wave with infinite distortion (clipping) becomes a square wave, so if you just kept turning up until the voltage stopped rising when measuring across a resistor, you'd over-estimate the power output of the amp.
Or you don't worry about it and just play.