I see. What I envision myself doing is, using the WiFI at home, contacting friends, arranging a time and place to meet, then going. More and more places have WiFI, and most of my friends have a WiFi spot. In Oregon it will become illegal in 2010-on to text while driving, so having a IpodTouch would keep me from checking it too often while driving, or carrying on converstations while I am driving. It is a nice way to bust up traffic by chatting on a phone, but it's simply not pratical or smart.
Also with companies like Clear providing WiFi in downtown Portland Oregon, and around Portland, having WiFI makes more sense than having a phone that crawls on the internet. While Clear is expensive at $50 a month for unlimited usage, at the moment, I expect that market to grow and monthly fees for unlimited WiFI will become cheaper.
A downside to being 'WiFI' only is not being able to use the ipod to get help if my car breaks down on the side of the road.
I started thinking this when I realized I could not properly use Twitter on the Tmobile Sidekick I have the 2008 version). I also have been with T moible for maybe 7 years. It gets redunant seeing Tmobile release a 'NEW' phone every 6 months, when they are clearly not pushing the sidekick to offer more things sooner, rather than waiting and waiting for T mobile/ Danger to actually make an attractive Sidekick. I got an ad for the Tmobile Motorola Cliq which looks nice, but I fear will have a hefty monthly price tag like the IPhone 3G does.