You're welcome. Glad to see you're getting it.
About the Grado spec, you got me! I would guess they mean 98 SPL @ 1 mW, since Grados are known for being fairly easy to drive.
In my understanding, current, voltage, or power output can be the limiting factor for an amplifier depending on the load, signal, and internal characteristics. I may have accidentally misled you into thinking that voltage was usually the limiting factor for headphones--really, it's that voltage is more of a concern than current. The physical reason why in most cases is unfortunately beyond my understanding. Maybe I should have taken more than the minimum number of electronics and power courses when getting my degree.
As far as I know, your summary of the speaker vs. headphones issue is usually correct.
I think the sensitivity (dB/mW) may be the more useful measurement in looking at amplifiers because most give some kind of max output power spec. Of course, max output power will depend on the load, and only sometimes will they give you the max power at impedance A, impedance B, and impedance C, etc. Also they tend to quote output power in different conditions, or with different levels of distortion...Really, the moral of the story is that there should be more standardization, with output power, SPL (/mW or /mV), frequency response specs, and the like.
To answer your question more directly, you still need to consider the impedance of the headphones; just efficiency or just sensitivity are not enough. Whether or not an amp is rated for a certain impedance or not isn't important I think. You can drive 600 ohm headphones with amps not spec'ed for that--it just might not be loud enough. An amp spec'ed for 300 ohms may not be enough for some 250 ohm headphones. Many op amps and the like aren't spec'ed below 600 ohms, yet people use them to drive IEMs.
Maybe the best illustration is a graph, so look at this graph I took from the datasheet for the Texas Instruments TPA6130. That chip is used as the power op amp in the output stage of the Fiio E5 and E7 amps. V_DD is the positive supply rail, while the other rail is 0 V. The device seems to be current limited at around 10 to 20 ohms load for that gain, but not so for higher loads.