Five "Golden Rules" of HiFi?

(1) If one waits for a product that one deems relevant for one's system...waiting for that product to meet a price (low/used) point but will not benefit you in the long run. Buy it, enjoy. Life's short!
(2) Buy what you perceive is in your best interests. Whether it's used or not...waiting could be forever, buying sooner will be beneficial for your own benefit plus you'll have more chance to listen to great music reproduced better in your own home!
(3) Buy lots of music!
(4) Read a lot. Listen a lot. Make your own decisions based upon your own experience!

I forgot... I have one more...
(5) Learn how to listen, learn what to listen for. (Maybe the most important of all).

Biomimetic the trouble with headphones (for me and I assume others as well) is that you can't get a soundstage. The performers aren't performing in front of you, they are in your head!  While this may sound like a good thing, I can't get used to it as I don't find it natural. 

OP-

all of your points taken except buying 2nd hand speakers. Nothing wrong w/ this practice so long as you trust the seller.

Yeah…go to the Munich High End show and note the cost of schlepping yourself there is more than you might spend on most components…no problemo! Coming from the school of Experienced Professional Live Sound Tech and Professional Musician plus certified old person Logic Driven Audio Freak (or simply, "EPLSTPMLDAF"), one suggestion is to clean yer ears with the ear wax cleaning kit from the local drug store…been using that stuff for years. Also, ignore the "audio mysticism" as it's utter nonsense…directional fuses, expensive feet for your gear (vibration from sound goes everywhere all the time…get over it…) except maybe to decouple your speakers from a wood floor (spikes don't do that, rubbery things do), and simply be logical about things…remember you have your own taste unless you're some sort of cowardly wimp, which is also OK as the unstable keep the commercial world revolving…listen to live concerts that only I mix as MY taste is impeccable (Julian Lage…miked his tiny old tweed amps and the bass as Wolleson wanted no mics)…there ya go!