Are advances in technology making speakers better?

In my environs cars are seen as accessories or jewelry even. "Nuff said.

Try to relax. Unless you dislike your sound then why be influenced to change? I have had my present loudspeakers 17 years and every once in a while I demo other speakers and have not found anything I really wanted to purchase. I greatly enjoy the sound I am still getting from my Von Schweikerts. Quality construction with a good design is timeless.

For me, the best therapy for Audiophilia Nervosa is to attend an audio show. I've been to two of them pre-covid (AXPONA & Tampa) and the Pacific Audio Fest (PAF) in July. This is where you can get a broad overview of new stuff and how it sounds.

In my case I'm running a pair of Thiel CS6 speakers, Velodyne sub, and a Krell KSA 300S amp with a Krell KRC2 preamp - all dating from the mid 90's.The rest of my system is nothing exotic (KI Ruby SACD, Blue Jeans cables). I can safely tell you that very few systems at the PAF, with many costing over 6 figures, sounded as good as my system. There were a few systems that outshined mine is tonality, detail, and imaging but I left most rooms thinking that my system sounded better. There were many rooms where the cabling was worth more than my entire system and the sound was certainly not spectacular compared to my system.

My answer to your original question is that, in my experience, audio has not come all that far in the last 30 years unless you spend big bucks. At AXPONA I heard a pair of Von Schweikert Ultra 11's ($325,000) in a system that was valued at over a million dollars. The sound was incredible and it was definitely better than my system in pretty much every way. But when I got home and played some of the same demo songs I was shocked at how well my system held up. The speakers that blew me away were MBL 101 E Mk II ($80k). This is one case where a different technology really is a step forward. IMO everyone should hear these speakers if they possibly can.

At PAF I made notes of which demo songs were played in which room and as I played those songs on my setup after I got home I was somewhat incredulous that most of the time my system sounded at least as good or better than systems costing hundreds of thousands of dollars. Yes, I know that show conditions are not great for demoing high end systems but my listening room is certainly nothing special (have no dedicated room treatment).

I'm a big proponent of going to an audio show if you can possibly swing it. It will exponentially expand your knowledge and experience base and it's just plain fun. If you really want to hear if all the hoopla around "new" audio technologies is justified it's the best way to do it.

Manufacturers have to replenish their lines for marketing reasons alone. The technology has not significantly improved or even changed in decades. 

Spend your money only if you are looking at a significant upgrade in performance, otherwise keep saving your money until you can do so or you will never get there. You should not budge until you can afford to spend at least three times what your current system cost and even then you have to be very careful not to make a sideways move. 

I have a friend who has a very very good system, his speakers are old Wharfedale, I always wonder how much more improvement he will get,  if he will upgrade his speakers? I once ask him ? If he is considering new speakers? He said never ? I like his response because he is happy with his speakers why change?