about the visorphone thing, Yes, you do use your minutes when you surf the net, and you do have to dial-up, which are definite minuses. But you can get one of their more expensive plans (depending on how much you use your phone, and how much you will be web surfing with your pda, and when) for like $40-$50/month, and you shouldn't ever run out of minutes. You can also sign up for free weekends, and other regional promotions that should keep your actual billed minutes down.
As far as looking ghetto talking into your pda, I agree, however if you buy a hands-free kit, it won't look quite as ghetto, and you'll be able to put anything into your pda (appointment, etc.) while you're talking.
I still don't think the thing is worth the $300 up front (and definitely not the $500 it will cost if you already have service), but it sounds like a better alternative to paying $80 or more per month for wireless modem and cell phone service.
Just my 2 kopeks.