With SineGen it is possible to readily switch between 2 sine tones with a click. OP should perhaps look into that?
EQ'ing is indeed very complicated and full of trade-offs no matter what method you use, there is really no practically achieveable ideal, though each method will have pros and cons. I do, however, find the JB method as recently discussed quite appealing in general. Pick your poison.
Even using reference speakers in a treated room can't be considered ideal if you seek fidelity (due to stereo crosstalk and phase issues for example, among other things), and when done fussing over that there's the source material to consider too, which will be sub-par as well, which makes it a moot point doing any better than a reference class speaker setup.
Sometimes I entertain myself by trying to design/think out the perfect fidelity situation when playing back recorded sound, and consider viable approximations. My idea of fun