Be Prepared! (A Wireless Addict's Toolbox)
Against my better judgement (and against my sincere wishes) I continue to find myself in airports, airplanes, and hotels far more often than I would like. Given that much of my work happens disconnected from my home network, and, to be honest, a connected computer is an entertaining computer, I feel totally out of touch when I can get connected to the internet. I may spend more then I should each month on connectivity ("may"?), but it works for me.
Although there are a ton of free wireless hotspots out there, and there are more every day, I find T-Mobile Hotspot to be worth the monthly fee. Almost every AA Admiral's Club has a drop, and just about every Starbucks, Borders Books, and lots of MacDonald's (not that I ever go into a MacDonald's except to take use the facilities) have them as well. The fees are somewhat steep ($29.99 per month with a year-long agreement, $39.99 per month without), but they support WPA for secure access at many sites, and their connection speeds are generally quite good. I didn't think I would use it all that often, but I do. And although only a single computer can be logged on concurrently, if you are generous and care to share your credentials, you could either get friends to pay you for temporary use when necessary, or you could just be generous and let friends use it on demand. (I make my friends call me first, to confirm that I'm not on the road and needing the service.) This may violate the license, but I can't see how they would care exactly who is using the account.
What about everywhere else? There are a number of cellular-based wireless services available. At this moment, none beats the service provided by Verizon Wireless, as far as I can tell. Contenders are arising, but Verizon's broadband service usually provides me with at least a DSL-speed download, and not-too-terrible upload speed. The faster broadband speed is available currently in around 30 markets (including most of the cities I ever go to), but in the rest of the country, you get at least reasonable speeds (about the same as Sprint's CDMA wireless service, and still a bit faster than Cingular's GSM-based service). That is, Verizon has you covered no matter where you go in the country, for the most part, and in 30 major markets, you'll get about the same speed as a normal DSL connection. Again, this isn't cheap ($79.99 per month), but I use it all the time. I sometimes use it at home, because both the DSL and cable connections at home are flaky. I use it in hotels that don't provide wireless access (or when I'm feeling too cheap to pay extra for it).
Finally, if I may, let me sing the praises of the best (at least, the smallest) Windows Mobile Smartphone out there--the Audiovox SMT6500 (If you're in the UK or elsewhere in the world, you can purchase this packaged as the Orange C500.) AT&T originally started selling this the week they got bought out by Cingular, and Cingular immediately dropped support for it. Fortunately, Cingular realized what a great phone this is, and started carrying it again. (Although it's a tossup between this phone and the Motorola MPx220, I happen to dislike flip phones with a passion, and among the geeks I hang out with, I see more of the "candy bar"-style Audiovox than I do the flip-phone Motorola. Your choice, however.) In any case, although the phone (and Windows Mobile) has a ton of features to praise, the one I use most is the Always Up To Date feature provided by Exchange 2003. For no extra service fees, Exchange sends the phone an SMS message when an email message arrives, and the phone wakes up, and synchs up over the airwaves with my Exchange Server. Yes, it's a little low-tech, but it works, and with an unlimited data plan with Cingular, I don't worry about the amount of stuff traveling over the airwaves. (When you travel out of the country, kids, make sure you turn this off. The costs become astronomical when you're paying by the byte!)
Yes, I probably pay way too much for connectivity (and I forgot to mention the DSL and cable bills at home). But I stay entertained, and connected. You may not want to go with all these services, but even one will help keep you connected most of the time.