I remember when I first got into the Squeezebox (long before Logitech bought Slimdevices). I had a real love/hate relationship with it, but truth be told, I loved it for what it was - a technology well before its time. It got me ripping all my CDs, managing flac files, worrying about metadata, and buying into the Squeezebox environment. I think at my peek, I had two SB3s, a Duet and two Touch. Came within a hair of buying a Transporter. It was a sad day when Logitech bought them, and far sadder when Logitech bailed a few years later. But LMS lived on and supported quite well in the public domain. It's only recently that the SB Touch started being sold on eBay for less than it's original list price.
When Roon announced that it supported playback through Squeezeboxen, I jumped in and never looked back. That was 3 years ago! Roon continues to make significant strides. I understand why many folks balk at buying in, but for me, the lifetime license was likely the best audio investment I've made. Never any headaches. It just works - whether streaming to my Squeezeboxes (which I still use), my iPhone & iPad, my Devialet Expert Pro, or through my headphone amp. I've got RoonServer running on my PC with all my music in flac files sitting on a 2TB drive routinely backed up into the cloud.
So, no nightmare here. Roon has made it extremely easy to just sit back and enjoy the music.