I'm surprised every year when my 160GB iPod classic doesn't die, but the failing hard drive and unreliable battery life makes me think it's nearing it's end. I started reading up on possible replacements a year ago, but it kept going. I'd love some recommendations with the following considerations: Listening habits and user interface: - I ride a bike 8 miles/day, 5 days/week, whether it's 100 degrees, 10 degrees, raining, sunny, or snowy. Build quality and a decent case are important to me. - I currently use relatively cheap ear buds when riding or walking somewhere because of the beating they take. I rarely use headphones, but am interested in checking some out eventually. - I will plug the player into my Jolida JD302CRC tube amp when I'm at home - I listen to full albums at a time almost exclusively - I don't stream music and I don't plan on it - I have one small bluetooth speaker, but I generally don't plan on using bluetooth - I don't own a car so I'll rarely have use this in a car. I imagine this is where bluetooth might come in handy - I don't care about watching videos on this (I have a phone after all) and generally don't need a large display or touch screen File Transfer and Management - I'd appreciate the ability to make playlists on the go - I have a 2013 MacBook pro and still use iTunes to manage my iPod Classic. The MBP has 2 USB 3 ports, 1 Thunderbolt port, and 1 SDXC card slot. - I have approximately 140GB of music, but mostly 320kbps. This will only grow so storage capacity is important, but most players seem fine. Budget: - Seeing as I'm going from something not-so-special, I'm fine going with a cheaper player and may notice a big jump in quality even in the $500 range - Ideally, my max budget is $1,000 for player and case I've generally narrowed the list to the following: Fiio X7II - $649 Fiio X5III - $376 Astell&Kern AK70 MKII - $699 Astell&Kern Kann - $999 Onkyo DP-X1A - $479 I was initially looking at the Fiio X5III initially, but reading the forums, I see people have a lot of firmware issues that Fiio doesn't seem to be very quick to address. I assume the X7II will suffer the same issues so that gives me pause when it comes to those products. Any thoughts on this would be much appreciated! Feel free to suggest other ideas or places to find these cheaper (I used Amazon to get a basic estimate).