Hey, sorry you ripped all those CDs to wav - it's an old standard that came about before tagging was implemented. I wasn't suggesting that you convert them to FLAC and then keep the wavs, I was saying you could convert them to FLAC (or another lossless taggable format) and then delete the wavs. That way you'd have files in a lossless format (like wav) that was taggable. That would keep you from having to re-rip everything - you could use a converter and do it in batches or possibly even all at once. You would still have to tag the files though. Then you can setup your computer so it plays FLAC and setup Ampache to transcode to mp3 for using it with mobile devices. There are different codecs to choose from - it just depends what you're trying to accomplish and how much flexibility you need. Probably the least problematic way is to rip everything to mp3 in id3v2.3 format - it's taggable and just about every player and device out there works with the codec and reads the tags.
Ripping them again but to a format that supports tags might actually save you time since the ripper should automatically tag the files with %artist%, %album%, %title%, and %track% which is a good starting point. Then when you run Picard on them, it has some tags to work with in addition to trying to find acoustic fingerprints.
It is a lot of work to get a music catalog in order. It won't get done overnight or in a couple of weeks. Start with a handful of albums, then try out some different tools on them with the goal of getting everything set. Make the folder hierarchy like: /MyMusicLibrary/Artist/Album. Make a Various Artists folder for compilations. Start out making sure you've organized the files into those correctly named folders. Then tag the files an album at a time. Once the files are tagged you can rename the files based on the tag information - for instance I like renaming files like:
%track% - %title%
There isn't much need IMO to put the artist or album in the filename if it's correctly filed in your folder hierarchy and the artist & album is embedded in the file as a tag.
Then add album art of your preferred dimensions - 500x500 is a decent compromise. I like larger art but this can be problematic when using Ampache with mobile devices that have limited bandwidth.
You could, of course, try a more automated approach - convert them and then see how well Picard identifies them when scanning. Or try Beets. You're going to want to play around with a few things to decide what's best in your case.