@realdeal99
I think you should keep a couple of things in mind:
You're ripping a sizable amount of cds (300). So, i think you should try to get things right the first time, than reach a point in the future where you say to yourself "damn i should have done it differently" and start ripping all over again.
With that said, i think the best way to go is to rip to some lossless format and either MP3 or AAC for your ipod. Now, i know people will say you can rip to X format (where X is usually OGG or MPC) and use Rockbox on your ipod. It's up to you... just remember that MP3 MAY require a larger size to become "transparent" when compared to the more modern encoders like AAC or OGG, but when you use the -V2 preset (check the HA wiki so this doesn't appear greek to you

), i can guarantee that MOST of your music will be transparent. Plus MP3 is natively supported EVERYWHERE. That to me is a HUGE bonus. No need to tweak around or twiddle with things if you need to get MP3 working

.
Now, you need to pick a lossless format. As you can see in the article called "LOSSLESS CODECS' in the HA wiki, there are a fair number of lossless codecs. However, I'd recommend you choose from one of:
* Flac: Has the most hardware support (in case you decide you need to play lossless files in your portable. why you'd want to do that is a different question

). However, Flac doesn't compress as well as the others in this list.
* Wavpack: Usually compresses better than flac, without being noticably slow to encode to or decode to. Is open source, is supported by a fair number of devices and programs.
* Tak: New kid on the block. This was the codec i used when i was ripping to lossless files. Has kickass compression, AND decodes fast. On the downside, is supported by few software programs and NO hardware at the moment. However, the codec is very new and will surely gain traction as time goes by.
Now ripping program. I know people have recommended foobar, but i think since it's something you do ONCE, you should use EAC. It's not rocket science. Print that guide and do as it says. As long as you can follow directions it shouldn't be difficult. However, an easier route might be to use dbpoweramp. Give the program a look if you decide you don't want EAC.
If i were you, i'd use EAC to rip to TAK. Then use foobar to convert all the TAK files to MP3. Or if you're bold enough, use REACT (see wiki for REACT guide) to rip to TAK AND MP3 at the same time!