It is a matter of taste, of course. If you want the most analytical detail, good headphones can't be beat. They also produce bass which is unaltered by room modes, thus often smoother and clearer in the bass. Speakers, by comparison, are much more expensive, require more space and fiddling. But a big, deep, reach out and touch sound stage and bone-rattling bass are too much fun. Unfortunately, you need EQ, good-sized and treated rooms to do it right.
Speakers vs. headphones
OK, desperation is setting in (I'll admit it). I have a 12-by-13 room with 7-foot ceilings (carpeted room and acoustic tiles up top) and I've tried every speaker and sub placement imaginable for my very modest system (NAD 326 amp, Totem Mites, Velodyne SL-800 sub). Even without the sub, I can't get the sound to anywhere near what I'd like it to be. I had an even more basic system (NHT Super Zeros, Onkyo amp, M&K sub) in my old home and it sounded INCREDIBLE compared to what I have now. Like I said, I've tried diagonal speaker placements and everything else, including room treatments (panels on first reflection points – no bass traps yet, but it seems the problems go well beyond bass). The question(s): Is it time for headphones? Is it even possible to get decent sound in a room with these dimensions?