I am a longtime Audible user. I started out with an iPod. The one with the circular thing on it. I still use that as my main unit and it stays in my car except when adding to it. I have an iPhone 4 with only 16gig. What I do when I'm flying for work is download the current book I'm listening to plus one. Then I delete it off the phone. When I upgrade to the iPhone 5 I may do away with the iPod. I have the audible app on my phone and iPad. The latter is a work device, but it is the same as the iPhone as far as ease of use. I've been doing this for almost 10 years and love it.
Books are easily added and removed through iTunes. I only keep the books I haven't read on the iPod. I also only read unabridged.
Before USB I used the lighter connect and radio. It was ok. I haven't had a cassette in years so don't know how they are anymore.
Hope that helps! I drive 40,000+ miles a year plus fly. I can't imagine doing without. Hopefully I will be down to one device in the near future. I imagine its going to be a phone!
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I have the iPad with the cellular capability. (We don't have the option of WiFi or cable internet where I live.) Even if we did, I think the cell connection is well worth the extra expense because you have access to a cell signal most places now, but a WiFi connection can sometimes be hard to find on the road.
HOWEVER, Audible will only download the first 50 MB (about 2 or 3 hours) of a book without a WiFi connection. You can listen to the partila download, but you'll need to find access to WiFi to finish downloading. So, you'd probably want to download the books for a trip ahead of time when you have a WiFi connection, but if you're on the road and have a sudden unexpected desire to hear War and Peace, you'll only be able to listen the first couple of hours before you have to find a McDonald's to download the rest.
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If you have an older vehicle that doesn't have bluetooth, your best option is to simply upgrade the radio/sound system. It's pretty easy, you can drive in to any Best Buy or other electronics store and they'll do it for you, or of course you can do it yourself if you're handy that way. We did that in my Dakota a couple of years ago... bluetooth wasn't standard yet but the unit we put in let you plug nearly anything in. I kept my iPod in the glove box, plugged in via a wire that they ran under the dash and into the back of the glove box, it was invisible and worked well. It always stayed charged, and I just brought it inside to synch when I finished a book.
The new 4Runner has buetooth: my iPhone syncs with it when I get in the car, and I can play music or audiobooks with the phone in my pocket or purse, very cool. I can plug it in if I need to charge it, there's a power outlet in the console.
If your audiobooks come from Audible or iTunes, they are stored in your account and you don't need to keep them stored at home, just keep what you're listening to on your device and delete the rest. If you really want the security of hard storage, and/or you have lots of stuff ripped from CD's or other sources, invest in an external hard drive. Mine is a terabyte and cost less than a hundred dollars. You can save a lot of stuff on there, LOL.
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Thanks everyone, lots of good information, some just reaffirmation but that is good information too. I was planning to get an IPad mini, after this discussion will probably get 32G, new truck not imminent but on the radar screen, the '06 is at 170K. Like being able to tap into the truck's audio system.