I recommend looking into JRiver for playback. Also, JRemote for your iPad.
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These are all free players that seem to be what you're asking for. I'll list them in order of what I think you will like the best.
Amarok, Clementine, Banshee, gmusic browser, Quod Libet, Exaile, XMBC, Nightingale, Audacious (No library function), Rythmbox.
They're all free, so you might as well try them all. Clementine is my personal favorite. Quod Libet is good for tagging.
I fall into the old and stupid basket too.
I find the Wiki instructions kind of fragmented, difficult to navigate and understand. Copying my CD's (I think Jriver calls it ripping) seems to be odd. I actually copy my CD's using itunes in lossless, since it is so much easier. I did one last week using Jriver and it was strange. Seemed to save it in a odd format as well. Monkey something? It also didnt tell me where it was going or what it was doing with the file. I found it after the rip, but not very laymen (that's me)friendly.
I'll give them a try - one at a time until I hit what suits me best.
As a side note, one must wonder how complicated is it to build a decent sounding, user friendly, moderately priced playing software?
Behemot (Threads | Answers | This Thread)"
None of the players were talking about hear are really difficult to use. I know you don't like the way Foobar looks, but I don't find it too difficult to use. I suspect you may be having trouble with using the library functions and tagging. If you don't know what you are doing, it can be frustrating. If you want to keep things simple, and don't mind using your file system to keep track of music, try Audacious. Its a very simple player with no library, but it plays every known audio format and does have a respectable set of features. Its a good solution if you are a classical music fan. People tend to find Classical very difficult to tag and manage. A different way to handle this type of music is to rip the entire album as one track with a Cue sheet. Its a good compromise to spending hours tagging every little detail.