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The value proposition is hard to take lightly. I've not regretted the lifetime membership but I'm usually blowing similar amounts or more on equipment so I kind of justified it that way.
I'm guessing it needs to be really good to have survived though. There are great music players around and some of the biggest names are free so its a tough market to be the most expensive player in.
Apparently the extra metadata costs them quite a bit. Can't remember the name of the company that supplies it but Allmusic is involved somehow.
Airhead
JRiver is a one off cost of $60, and if you want to upgrade to future releases you get something like a 50% discount. I've been using it for over 10 years and I'd guess it's cost me less than a year of Roon, which is why I think Roon doesn't seem like great value.
I doubt that'll stop me though.