"So, which handheld computer should I buy?" I wish I had a nickel for every time I've been asked this deceptively complex question. It's often couched in terms of Palm vs. Pocket PC, making it even harder to answer without copping out ("Buy what you like.") or sounding biased ("Buy what I have.") I recently typed out a quick response to this age-old question in PDAMD.com's discussion forum, and it appears to have struck a chord with some users, who have added their own twist to my comments. Since my original intent was to try to give a non-biased answer, I'm reposting my response below, with an added bit on battery life and memory at the end (I should've included that before).
"So, which handheld computer should I buy?"
Basically, it boils down to a few decision points:
1) Cost - How much are you willing/able to spend? Bear in mind that most handhelds have a 1-2 year lifespan, tops.
2) Size - How much are you willing/able to carry around? If you don't have your handheld with you, it won't do you any good. Make sure that you can carry your handheld virtually anywhere you go comfortably. Not everyone wants to wear a belt-clip case.
3) Color/No color - Although this doesn't really help you in the Palm vs. Pocket PC decision, it can narrow down the number of models you're considering. Ask yourself whether you really need color, or if it's just a luxury (Note: I used to dismiss the value of color since most of my medical references are text-only. However, I really like my new Palm m505. Is color necessary? Not really. Is it nice? Definitely.)
4) Software availability - this is really one of the most important points, since your handheld is merely an expensive paperweight if it doesn't do what you bought it to do. The Palm platform definitely has the advantage in terms of the sheer number of applications available, not to mention the large number of excellent freeware programs out there. Pocket PC users have fewer programs to choose from, although most of the major categories of applications are represented. Check sites like the Ectopic Brain and MedicalPocketPC.com to get an idea of what's out there for Palm and PocketPC respectively. The bottom line is, what do you want your handheld computer to do (realistically)?
5) What do your friends/coworkers use? - This isn't a trivial point either, especially if you're new to handhelds. Not that there's anything wrong with being different, but you may find it harder to get help and share files and applications.
6) Do you want to write your own programs? - If so, explore the various options available on both platforms. It's always been far easier to write for the Palm platform, which is one big reason why there's so much more software. Not that it's impossible to write for Pocket PC, but plan on spending more time and money doing it, and having fewer development environments to choose from.
7) Batteries - Many handhelds, particularly color devices, use rechargeable batteries. Others, mostly grayscale Palm OS devices, use replaceable batteries. Battery life in actual use can vary anywhere from a few hours to several days. Make sure the device you choose fits in with your own usage patterns so that you don't find yourself with dead batteries in the middle of your workday. This is especially relevant if your workday sometimes lasts as long as 36 hours, as it sometimes does in medical school, residency, or any other time you take overnight call.
8) Memory - It's difficult to compare Palm OS devices to Pocket PCs based on their built-in memory, since Pocket PCs need more memory than Palm OS devices to accomplish basically the same thing. This has to do with operating system overhead as well as the size of typical applications and files. However, be sure to buy as much memory as you're likely to need, regardless of which platform you settle on. For Palm OS devices, nothing less than 8MB will do, and most users will appreciate the 16MB included in some newer models. Most Pocket PCs include 32-64MB of RAM. Built-in memory is less important than it used to be now that most devices offer memory expansion via removable cards of various types (Compact Flash, Secure Digital, MultiMedia Card, Memory Stick, Springboard, etc.) If you plan to run lots of medical reference software, be sure to pick a device that includes an expansion slot. Some devices, such as the Handspring Visor Edge and the original Compaq iPaq, require a bulky adapter in order to take advantage of expansion cards. A follow-on question might be, "Which expansion card technology should I go with?" This is less important overall than choosing the right device, since most good software will support all of the current expansion card types. However, the cost per megabyte can vary significantly from one card type to another, so do a little comparision shopping before you buy.