I'm currently running all around, and I've found that it's still a pain to stay connected when you're on the road. Hotels have cumbersome wireless access, there's a lack of wired access, you have to pay sometimes, the signal can be weak or incompatible, and so on. I just wish business owners would start seeing how much of a benefit you could provide to your customers if you offer free wireless without any intrusive sign-ups or anything like that. Or better yet (though it's a substantial infrastructure investment), provide ethernet jacks in every room.
Although, there still is the problem of security. I'm sure I always overreact and there really aren't people sitting in the parking lot sniffing passwords, but I still know how easy it is to do and I'm always wary of what data I put out there on open networks. Right now I'm running off of Verizon's EVDO network through a USB connection with my phone, and that tends to solve all of those problems, but there still should be additional focus on all of these issues (and specifically security will be one that people will be increasingly worried about into the next five years).