Microsoft makes Wi-Fi one of PocketPC's centerpieces: Although PocketPCs were well in advance of Palm's Wi-Fi connectivity, Microsoft never seemed to seize this advantage by offering tools to make it easy to connect to Wi-Fi networks. I owned a Toshiba e740 with integrated Wi-Fi for a few months, but sold it because it was so frustrating to roam and connect with it. Finding networks, entering keys, managing the process -- lightyears of pain away from Windows XP's relative ease.
Also, like XP, the PocketPC software lacked a profile manager or location manager: each time you switched networks, you had to re-enter information. Boingo released a client for PocketPC, but it only supported certain models. (Also, Boingo has changed its zero-cost approach: to sign up for Boingo, you have to pay $7.95, which includes two initial connection sessions, so you can no longer just use Boingo as your profile manager without that ponying up.)
Microsoft's announcement today of the Windows Mobile 2003 software for PocketPC is an attempt to make the connection process as simple as it should be. The new client supports all the doodads necessarily for corporate connections, including VPN support and 802.1x client configuration. It looks like it might support multiple network profiles, but the information on the site is scanty and the so-called demo doesn't elaborate much.
Part of the launch includes promotions with T-Mobile, Wayport, and Boingo for 30 days free service. It would almost be worth buying a PocketPC for the month and signing up on all three services to test them out -- just remember to cancel before 30 days is up! The free offer pages for each service don't list any limitations on top of "free." (One site I visited recently defines "unlimited" as 150 connections per month.)
Boingo released a beta of its Boingo Software for Windows Mobile 2003 today.