I started my re-rip process with some dedicated program that I ended up abandoning after seeing how easy it was in Foobar. You can open the CD and rip it from there with accuraterip verification. You can save your specific options, so future rips are just a couple clicks.
Afterwards, I like to complete my tagging with audioshell. For me, it's a two-step process, but it's not complicated.
I also tend to go back to Foobar to transcode my FLAC to MP3, for use in my car.
For audio files there's a lot of options. You can try mp3tag for a standalone program or AudioShell for a context menu addon. For pictures maybe something like that.
If you don't want a full blown media library player alternative, try AudioShell which is a context menu extension with plenty of capabilities.
MusicBee is the best free library manager and player out there by far.