I think there is one way the new speakers will win big in the comparison, and that is with the "equivalent prices" stipulation of the opening post. In the past, audio gear was very expensive, which is somewhat obscured by the fact of inflation. Here is an inflation calculator one can use:
Inflation Calculator: Bureau of Labor Statistics
To give some examples:
$100 in 1960 is about $788.86 in 2013.
$100 in 1970 is about $601.81 in 2013.
$100 in 1980 is about $283.38 in 2013.
$100 in 1990 is about $178.66 in 2013.
$100 in 2000 is about $135.60 in 2013.
(I hope I have copied the numbers correctly; I recommend using the calculator rather than trusting the numbers listed above, which are there to give you the idea of what is going on.)
Plug in the list price of an old speaker into the calculator for its year, and you will likely be amazed at how expensive the things were.
So, when comparing an old speaker against a new one, the old one of equivalent sound quality is most likely going to have been far more expensive. Of course, buying used, one might be able to get the old one for much less than the new one, depending on what deals one can find.
Also, I think that, overall, speakers have gotten better, though some old ones are quite good, and consequently, someone owning such a speaker may well have no desire to buy anything new.
I tend to like the styling of some of the old speakers more, as many were made with rich, warm wood finishes that seem less common these days. But, of course, it depends on which speakers we are considering, as there have always been ugly speakers.