I have a large library of FLAC files which I use with my Squeezecenter setup at home to listen to lossless audio. However, FLAC or ALAC are just far too large to have on a portable device.
I really want to create and maintain a parallel library with ALL tags intact and I want it to be AAC (or rather M4A for iPod compatibility). It was very easy to create a parallel MP3 library with tags and album art intact using Mediamonkey. In fact it was so easy to create and maintenance is nearly automatic since I use the "device sync" feature of Mediamonkey but instead of a device I use a created drive letter that links to my MP3 "sync" folder. So the software automatically compares the 2 locations and will even create new MP3 files if I add new FLACs to the main library. The tags and album art were preserved.
When it comes to AAC it seems very difficult. I tried DBpoweramp using NERO AAC (I want to use only Nero since I believe it is the best AAC encoder). It failed miserably, and didn't write any tags. Needless to say I will not be purchasing that software.
I did a test with Foobar2000 using Nero AAC again and while the tags carry over, the album art does not.
Firstly, I am confused about whether FLAC files can hold album art in their tags. Some people say there are 2 kinds of tags in a FLAC file. One is the ID3 tag which apparently in FLACs does not hold any album art information. The other is the Ogg tag, which I believe holds Album art information. MediaMonkey seems to read these and display the album art, it also created a folder.jpg file in each folder for each album.
Now foobar, probably does not read the ID3 tag and it probably does not recognize the folder.jpg file. In fact it's conversion output options are primitive in that I cannot specify it to mirror the folder structure of the original files (album artist\album\track name.flac). It offers me no such options and will dump all of them into a single folder, so using folder.jpg files is not an option here.
MediaMonkey would be great but it does not work with Nero AAC. If it did, I wouldn't bother using anything else since it just handles files and formats like no other program. Foobar too is excellent but it does not seem to offer the level of customization as MediaMonkey in terms of folder structure. It does read the album art and might be reading the tag or the folder.jpg but it fails to read them or carry over that information when converting formats.
I'm really hoping I'm not the first person to do this and that someone has suggestions or a solution to keep parallel libraries of Flac and AAC.

