I’ve only ever been on a flight once where Wifi was offered (And it didn’t work on the return journey) It’s not offered on many short haul flights in Europe. And long haul flights sometimes charge an extreme amount for wifi And again reliability not that good.I don’t know where you travel, but I travel all over the US multiple times a month usually and I don’t have issues with WiFi in hotels or planes. Plane wireless is not blazing fast, but it’s enough to buffer some music. If you have a 64GB or larger iPhone I don’t see how you can’t load it up with enough music in advance of the flight to get you through it. I usually have stuff locally just in case the wireless is down on the plane. Even at the height of the iPod days I couldn’t fit my entire collection on one, so I’ve never been accustomed to having my entire collection with me. SanDisk and Sony are the only players I know of that are still around that can take SD cards. The larger Sony players are $$$$. The reality is the more time that passes the fewer standalone options there will be.
plenty of hotels in Southern Europe are still wifi only avaliable in public areas of the hotel not in your room. I find that a pain so currently go to a hotel that has wifi in the room