Smart move! When I first started in the Napster days, 8 or 9 years ago, there was no good way to organize stuff and I didn't pay too much attention to it. Big mistake! Took me hundreds of hours and a few weekends of nonstop work to get my library in pristine organizational condition. And it stays that way to this day. I find that with the proper organization, you can import your library into any program and it will be sorted correctly giving you flexibility and ease of use.
More music is always a good thing. And there are times when a proper playlist is indispensable (like the gym). But I've found that playlist listening will never replace full listening sessions with a full album run through. I, for one, am a firm believer that albums were meant to be listened all the way through, especially the classics. An experience, if you will, instead of a distraction. Cliched, I know, but true nonetheless.