More expensive = better?

No for sure not. Sometimes worse, cost seems to have little factor on sound quality sometimes. Always listen with your own ears and look at the measurements for a sanity check. 1/2 these products are snake oil.
 

I can think of a bunch of speakers that are made super nice but have bad crossover choices (odd slops, passed after cone breakup, etc) and will never sound right. Most electronics are good these days. If you want something that looks nice or is super powerful go for it but know what you are paying for is looks or headroom you don’t need. I am ok with that personally but keep my head grounded. 

Just moved from Bluesound Powenode 2i to NAD M33.  Along with switching from $20 generic cable from Amazon to Black Cat Cable CopperZone FLATWAVE speaker cable.  I have tears in my eye.

I was thinking about Hegel H590, how much better it is than the M33, I can't be sure.  Those who have heard both said H590 is better, at double the cost and much less functionality also.

In the end, you just have to make peace with it and be happy with your choices, otherwise, you will be chasing ghosts.

At some point some audio equipment became either Art, Or a fashon statement, or both. Your pretty $6000 speaker wire sure sounds nice. I'm sure glad I went to school to learn about such things. 

You have to compare apples to apples. Price can reflect things such as built-in DAC card, phono section and/or headphone. The casework can add extra cost (engraving, anodizing, finish, CNC artwork, etc.).  Also, if it is sold direct it's about half the price a dealer would charge. Can't really generalize an answer on a dollar for dollar basis with respect to sound quality.

always

as in, 100% percent of the time

😉