Answer:
)1 Ya you can do that, but EQ'ed ah, well, unless you have a 27 band equalizer (1/3 octave) and a test CD to measure frequencies with a sound level meter (Radio Shack use to sell one) and even with that it will still be subjective from the mic that picks up each frequency in the sound level meter, then the human ear chart for frequencies and loudness at which is played and anything else that is included before it suppose to sound good to you.
2) Ya, you can use headphones, I find ear buds to sound better than same priced headphones.
3) Your pick at the store, I like JBL, and since I do not have active monitors supposedly made for hearing (with correction built in like the two-way JBL monitors at $1559 for a pair)
http://www.sweetwater.com/store/detail/LSR4328Ppak/ I usually end up mucking it up, but listen to the stereo, headphones - and ear buds, and computer speakers and still muck it up, but I am learning and hanging around here found out some things I did not realize I had before. (like my RME unit has a Digicheck which shows the frequencies as they are playing coming out of the computer which I should have been using all along and probably should correct anything I have done, but there is always the next song I guess.
Live and Learn.
I figure none of it is perfect and since I done sound checking since vinyl days (sound level meter) that everyone hears different, every system is different, and all will sound different, but if it sounds almost alright through everything than I guess that is closer or as close as I may get even having the option of better equipment, unless someone wants to build me a $million dollar something or so studio like this one - Blackbird Studio C perhaps:
http://www.youtube.com/watch?v=exQRfHbSwn0 and that is only one of the 4 studios there.