For the time being forget about quality, price and other issues that are generally used to probe the popularity of a product.
Here are some notes from interviews of nine teenagers. It isn't enough to be scientific, but since the interviews were conducted separately, there may be some directional signals. Real studies would be very interesting.
The kids were from two upper income towns. The ages were 14 to 17. Six girls and three boys. All of the kids had portable CD players, 7 had cellphones, 6 had their own PCs (all nine only used Windows).
one girl had an iPod (a pink mini), six of the other kids wanted an iPod, one boy thought portable players were silly, one girl was happy with her CD player
two thought they would get an iPod for Christmas
if given a non-iPod mp3 player, three said they would eBay the device and buy an iPod on their own
one of them (the girl with the iPod) thought buying music from an online store made sense
three of the nine could correctly name a competing hard disk player
four would be happy with an iPod that held eight hours of music if it cost less (price not tested)
seven of them trade mp3s with friends
two thought that combining a mp3 player with a cellphone was a good idea, three were negative
eight of them said their PCs were frustrating to use
when asked about using players based on Microsoft's format, six volunteered they had heard Microsoft and the record companies can track what is on your machine and using this format was too dangerous
The last comment was particularly interesting. It could be confined to a small geographic area, but if it is widespread, selling Windows Media based players to pre-college kids may be more difficult than anyone suspects. One is reminded of the old spider egg stories that preteens used to pass around. It would be very interesting to see if their frustration with the Windows experience (which appears to be with malware and general stability problems) is coupled with this mistrust - if so, Apple has a significant opportunity.
The lust factor was significantly stronger in this group than college students we've interviewed, but remember that this is not large enough or carefully sampled enough to allow serious conclusions - it merely raises questions.
A trip to the periodical section of a well stocked library in pursuit of past visions of the future is great fun. Visions of the future speak volumes about the period the visions were created and most of them are far from the reality that unfolded. The futures being discussed today in places like Wired will be great sport in the future, so save them for your grandchildren.
Transportation is great sport as it has fueled the imagination for well over a century. The intelligent and pneumatic transportation sections of this site are particularly interesting. Sometimes they get it partly right - the "suv" shown was drawn around 1911. I'm sure it would sell well today.
I've seen three very different groups deal with the consumerism of the late December holidays. Some fundamentalist Christians try to keep the "Christ in Christmas" and ignore or limit the secular part of the holiday. Another group tries to limit total spending as a response to consumerism.
The smallest, and most interesting group I've encountered, are the creative elite. There are families that have rules that you have to make the gifts you give. Of course most of us are sufficiently dull that this is an instant non-starter, but I have friends who give paintings, short stories, newly composed piano trios, handmade ornaments, homemade maple syrup and any number of wonderful things.
I have tried and failed over the years and generally rely on what comes from someone else's hands through my pocket. (er .. that sounds strange, but you get the idea). I recommend picking one person on your list and trying something.
Another way of approaching this to hire (if you have money) or partner with (if you don't) and artisan. A few years ago I designed a different sort of kaleidoscope for a major birthday present and gave the design rights to the artist in return for the prototype. A friend makes wonderful medals. Artists and musicians are frequently in need of money and, assuming there is enough lead time, can be engaged for that present of a lifetime.
If you do give commercial items, give things that enhance the creativity of the recipient. Most people are terrible musicians, photographers and artists, but it is much more satisfying doing something yourself than merely consuming.
Earphones make a huge difference. I've love my Etymotics and have listened to the low and midrange Shures (the $200 midrange phones are very nice, but I'm already happy with something less spendy). Some people hate in-the-ear devices, so you want to try audition these things - particularly if they are expensive.
If you have an extra bright sock laying around you can be very trendy.
iPodderX - probably the best rss podcast client. This area is developing rapidly, so you might want to look around.
iSight a great little webcam (assuming you have someone to chat with)
Airport Express - our iBooks now control our stereo. We stream our music libraries and net based radio stations. It just works.
12" iBook G4. Both Sukie and I have them and the laptops are in constant use. The iBook is the perfect size for packing around, has decent power to run what you need on a laptop, has over four hours of battery life and goes for about $1000. The G3 iBook was a trouble-prone dog, but most of the feedback I've had is the current G4 is solid. Add more memory and seriously think about AppleCare (you should think about a service contract with any laptop).
PowerMate - a wonderful programmable analog control. Trust me, this is wonderful.
More memory. OS X loves RAM. I would consider 512 MB minimal and recommend more. Crucial is my favorite supplier. I have never had a problem with them. The adventerous can find better prices on dealram.
USB pendrives. Incredibly handy for machine to machine file transfer and the floppy disk of the day. Dealram will point you towards the deals. It is very easy to get 1 GB drives for less than $80 these days.
An inexpensive miniDV camcorder. iMovie is a fine application for learning the basics of video and you can find nice cams in the $300 to $500 range these days. If the person already has a camcorder and has done some editing, Final Cut Express is an amazing tool.
Cases and bags by Waterfield. I haven't found anything better