Is new better than old?

I have been looking at upgrading my speakers. I have a budget of around $1,200. There is a plethora of speakers on A’gon and C’list in that range. I did a search of Full Speakers priced between $900 and $1,300 and got a list of over 100 really nice (or not) speakers.

My question is, are the newer speakers in this price range better than the older speakers in this range? Are the newer models with the latest and greatest technology, research and design likely to sound better that a speaker that is 6 or 8 to 12 years old, but when new was twice the price (or more)?

A good example is the 13 year old Vandersteen 3A’s vs two year old Paradigm Studio 60 v4’s. Both of these are around $1,000.

Another example is the Von Schweikert Gen: II at $1,099 vs new ERA D14 at $1,100 (seller says these are half price).

I may not be comparing apples to apples above, but I think you get my point. Is a speaker that cost $4,000 but is 10 – 12 years old better than a two year old speaker that maybe sold for $2,000 when new?

Thanks