Best way to store music

[RichManPoorManBeggarmanThief]

Please help a luddite in distress. I have the following things at my disposal

• An iphone 4S
• An i-mac
• A macbook air
• A massive external hard drive for a mac
• An ipod nano which is sync'd to a laptop (pc) which died about a year ago so the music files no longer exist except on the nano.
• A docking station/speakers for an iphone/ipod

What I want to do is get all the music from all my CDs onto one device (plus any downloads that I buy) and then be able to put it on a ipod/iphone when I want to listen to them via (I guess) itunes. Then I can chuck the cds and free up a lot of cupboard space.

What is the best way to go about it? I am sick of doing it and then the thing the music files is on breaking and I have a fear of getting rid of the CDs and then losing the files. Also, Can I unsync the ipod from the dead computer?

Finally, is there any point in using the ipod if I have an iphone, other than the fact it's smaller and lighter?

So basically, what's the best and safest way to store music files digitally? What would a geek do? . Should I use Cloud?

Personally I would always keep the CDs. I'm a big techie and I love my gadgets, but I simply don't trust virtual media. When I buy a CD I know it's gonna last until I break it or lose it. With MP3s, all other seems to take is a dodgy hard drive and you can lose an entire collection. This is especially risky with Apple products because of the way they give you very little control around how you store and sync music to devices.

However, if I had to chuck the discs, I'd be ripping them all to my PC, backing them up on an external hard drive and then re-copying from that drive to my laptop. Sounds excessive, but I've had two drives fail on me at the same time before so I wouldn't be taking any risks!

I'd burn them onto dvds and keep them on at least one hard drive and if possible a usb stick.

Thanks. Thats kind of what I was thinking, but then everyone seems to be just downloading straight to device so I was thinking I was just behind the times. Seems not.