I've read a lot of interesting ideas here but i'm afraid many are missing the point.
The OP wants an easy way to digitalise his music collection and be able to play it on several different devices, now and in the future.
Here's my 2 cents:
1) NEVER EVER get rid of the original CD's!!!
For one, the originals have the highest quality sound. For two: if your HD drive dies, you still have the original. And third: the CD's are proof you actually own the music! (I'll get back to this later)
2) Choose the most universal digital music format there is. MP3's format will play on just about every soft and hardware device around without having to convert it to other formats.
Personally i'd go with MP3 VBR 192kbps. The file-size is small enough so you can stream it over the internet when on holidays, and it is still high quality (unless you're an audiophile and/or your speakers cost a grant each you won't notice the difference with the original
In the the past I've allways used CDEX to rip cd's to computer. It's a tiny freeware, open source program, quick and pretty easy to use, but maybe there's newer and more user-friendly around...
3) After spending hours and hours ripping and organising your music collection: Make a backup! They don't make HDD's like they used to and about 5% die within 3 years. Store that backup HDD (together with your photo's and important home-video's) in a cool, dry place (preferably offsite --> in case of flood or fire
4) Choose a decent NAS and/or a decent Mediaplayer. The NAS will allow you to stream or upload your music collection to just about any device. (Personaly I have a Synology DS212 at home that allows me to listen to any of my songs anywhere in the world, on any pc, smartphone, tablet ... it did take me a while to set it up but it hasn't let me down
The Mediaplayer (Dune HD/Popcorn Hour/PS3/...) connected to your TV/Stereo/Surround can also double as a game- and videostation
There's many, many alternatives out there these days, but choose wisely!
And just to be complete: I started out years ago ripping my (huge) cd-collection to the computer but gave up after a while. There's an alternative way of getting music onto your computer and as long as you own the original cd's it is 100% legal. I'll just give you 2 words: "utorrent" and "discography". Just google the rest