From Viola: My questions are: will I really have to pay 99 cents for every song I load onto it...
No. In point of fact if you are, shall we phrase this delicately, a casual observer of copyright law, you won't have to pay a dime.
V: I was envisioning a roster of my 300 favorite songs.
Any player, ipod or not, will handle 300 songs with ease. Take your entire CD collection and go from there. I have several thousand songs on my iPod and there's room left over.
V: I've been told I can upload what I already own; can I upload songs from CDs I get at the library?
Yeah, well, here's the rub. Literally, the answer to your question is Yes, given the required technical knowledge, you are able to upload songs you already own on CD as well as songs from CDs you borrow.
The music industry knows this and doesn't like it. The music industry believes that making a legitimate copy for your own private use of something you already own is unreasonable, and that you should purchase a brand new copy of the music instead of making your own copy. There's probably five or six terabytes of argument and flame war about this subject, and that's the compressed version.
V: And if that's possible, what's to prevent everyone from downloading stuff from Youtube (new releases), burning them onto CDs, and then loading them onto the iPod?
Not much. Check Copyright infringement and DRM. Even if the recording is protected by DRM, there are any number of programs available that strip the DRM from music or video.
V: If I get it all set up the way I want it (a playlist for vigorous exercise, a playlist for long boring drives, etc.) it seems like I might be shelling out hundreds of dollars...
Yeah, doesn't it though? The music industry likes that idea of shelling out hundreds.
Occasionally the government will land on someone for copyright violations like the one you're referring to. Usually it's a dead broke college student or a senior citizen trying to exist on Social Security. They'll kick in the door, kill the dog and use their Taser on your nuts until you stop resisting, then you get taken to jail where you're stuffed into GenPop with the rest of the drunks, druggies and violent thugs waiting for court to start. The paper covers the story, the alleged violator pleads out and is fined over a million dollars by the government, and that's about it. Welcome to the US of A.
Here's a tip: Don't get caught.
Here's another: You'll end up making new playlists on a regular basis. I must have a couple dozen or so on my iPod. Therefore, making a playlist is a skill you'll want to acquire. You'll also end up adding songs from a CD to your iPod, which is dead easy. If you do, I suggest that you add the songs in MP3 format rather than the Crapple format, the reason being is that MP3 is easier to transfer from one system to another.
Final tip: When you connect the iPod to your PC, connect it up as an external drive. This prevents (to a certain extent) Apple from controlling your iPod. Which, by the way, can end up with you losing all the music on your iPod when Crapple decides that's it's all been pirated. Yo-ho.