Battery Life/Charging
Most people travel with a laptop. For those people, the Shuffle will be easy to charge. In my own case, I'm rarely away from my laptop for more than 8 hours, even including the time I spend sleeping. If someone intends to bring along a laptop, charging is easy.
For those who do not bring along a laptop, they can use the external battery pack or charger if needed. It's $30, but the savings will be made up in not having to buy batteries for a player that uses AAAs.
At $.50 each, and 20 hours per battery, the break even point, when the user has spent $30 on batteries, is 1200 hours of use. That's about one year. $.50 is fairly cheap for batteries, I think. You'd have to buy in bulk to get that price. WalMart sells them for $.68 ea.

White Headphones
If someone will be using the iPod on a plane, they'll certainly be using a different pair of headphones. The white earbuds, while adequate, are probably not the best choice for certain environments, such as while exercising or on a plane. They'll do the trick on a subway or at the office, but one would probably want something better for plane use. This would go for any MP3 player, for that matter. If you asked all the adults out there, I think you'll find the vast majority aren't wearing the white earbuds as a "fashion statement".

Newsflash- Dragging and dropping is not user friendly. It's kludgey and time consuming.
Here's what is user-friendly: plug it in, 3 clicks, 30 seconds. The Shuffle is loaded. Play music.
In 6 clicks you can customize to have the shuffle loaded with the least listened to music in your library, or all of your audiobooks, or all of your 60's music, or everything by a certain 3 artists, or everything from a certain genre, or all the songs you ranked the highest. You get the idea.

2 hours charging
I think most people with a Shuffle will be in front of a computer for a couple of hours for every 12 hours of play. This is really not much of an issue. For the rare user that may have an issue with it, there are alternatives that are as cost effective as using AAA-powered players ($30 wall chargers, $20 car chargers)

Nice perks
Audio Book compatible- If you stop the player, the book starts playing where you left off next time you hit play.
Plenty of accessories, including clips, water-resistant cases, external speakers, car chargers, skins, FM adapters, etc
It's one of the cheapest available for the capacity and features you get
Compatibility with iTunes and purchases from both Audible and the iTunes Music Store
Ability to easily adjust how much capacity is used for flash memory and how much is dedicated to music. This makes it easy to auto-load the player with the amount of music you desire, without breaking into any room you'd like to reserve for storage.
Compatibility with MP3, WMA (non-DRM), AAC (non-DRM and DRM), WAV, AIFF and Apple Lossless, as well as Audible's format (I forget its extension)