I spent about $30 and in a hours time had a aux input in my Ford Ranger.
With a stock stereo I installed a modulator that sits between the radio and the antenna.
The shuffle works great with the podcasts I download or mp3's I have ripped from CDs I own.

Having said that I absolutely welcome apple going drm free. They will get more of my business overtime instead of Amazon.

I purchased 2 small form factor USB external hard drives. I encrypted both with truecrypt. Since I am a Windows user I use MS's SyncToy to 'backup' the stuff I want to them. Synctoy makes it easy for me. One hard drive sits at work plugged into my PC, one at a bank in a safe deposit box. If my home computer dies and I need access to my data, I VPN into work and mount the encrypted drive or go to the bank and pick the other one up. I have a routine where on a set schedule I take the one from work to the bank and swap it out with the one in the safe deposit box. I take that one, synch up my data and then take it to work.

If one of the hard drive dies I still have the data at home plus on the other external hard drive. If one of the drives dies after the 5 year warranty period ends then I will buy another drive. If USB starts to become obsolete I would save some money up and buy 2 more drives that uses whatever technology we will be using then.

You don't know what technology we will be using to access data 10 or 20 years from now. Use what you think will be around and change later if that turns out not to be the case.