At what point do you...

There’s intangables at play here.

Only you can place the "correct" monetary value of the experience of new vs used. While "the math works" on (credible) used gear, assigning a value to the emotional attachment of breaking the seal on new gear that has not be touched by human hands since it left the factory is purely subjective. Owning new equipment vs taking possession of something after someone, or someones, have had their way with it may be a strong motivator for some. And, that "Christmas morning" feeling of the big reveal where you glance upon something special that is uniqely yours is difficult to access in dollars and cents (sense?).

"Still contemplating those NRG’s. I have until today as they’re also offering an extra 10% until tomorrow..."

Go for it big spender!!

Muriel Cigars TV commercial classics, Edie Adams singing ’Hey Big Spender!’ in 4 versions (lyrics in description) - maybe the greatest cigar television commercials ever made - video Dailymotion

@Yogiboy.    How about the Noxzema shave cream ad, Take it off, take it all off.

Given that higher end audio equipment should last 20 - 30 years (or longer) why should we be concerned about something that is 2 years old?  Or better yet, something that has been used as a demo in a dealer's showroom and is coming to me with full warranty?  The cost savings can be 25% - 50%.  I don't buy pre-loved to save money, but to allow the purchase of equipment I would have felt guilty paying full price for.  The same reason I like to buy cars that are two years old.  I am happy to let someone else pay 30% of the cost for the thrill of driving it off the lot.  Of course there are exceptions.  Soundlab speakers weren't option used but I still drove a hard bargain on a new pair.  I suppose in the end, I find it hard to respect people who have no respect for money.  I worked far too hard for mine to treat it frivolously.  But that's just me.  Spend yours anyway you want.  Cheers.

bigtwin  One of the reasons that I avoid buying used is because some things require a proper brake in period and there is no way to know how that item was treated and if it was properly broken in.

A proper break in period will determine the longevity of an item and only the original owner knows how something was broken in. Some people take a brand-new car and rag it from day one.  The next buyer of that car will end up with a car that perhaps will only last half as long as it would have had it not been mistreated. 

So, in the end, when considering how many years it has left, would the buyer of that used car really be saving any money? No.  That buyer would actually lose money when you do a cost of ownership analysis over the lifespan of that car.

This is why I don't buy used, particularly speakers, cars or items that should go through a proper break in period, but to each their own...