I want Nexrad and satellite imagery and METARs and TAFs live on my PDA
while I'm flying, like I now have them on the ground when I'm near a
wi-fi connection. How long will it be until I can get wireless voice
and internet connectivity that's legal for use in the air?

Maybe when it comes it'll look something like this:

N.D. to Test Balloons for Cellular Service
http://www.breitbart.com/news/2006/01/30/D8FF53180.html

If the cell sites are above aircraft, the presumed problems with the
current setup that are the reason for the current FCC ban on digital
cell-phone use during Part 91 flying would no longer be a factor,
right?

My favorite part:

------
The balloons swell from six feet in diameter to 30 feet after they gain
altitude. Once a balloon leaves the state, its toaster-size
communications pod would jettison, deploy a parachute and fall to
earth, where it would signal its position.

"We'd pay some guy a bounty, put in a new battery pack and send it off
again," Knoblach said. Schafer said the repeater could be used
indefinitely "unless it lands in a lake or gets run over by a truck."
------

Watch out for electronics falling from 100k ft.! Will there be
"falling communication equipment TFRs"? Or rising for that matter?
And the article never mentions what happens to the envelope of the
balloon!

My wireless phone has bluetooth capability. It would make a great
modem to connect my PDA to the internet and it would solve my problem
today if I could operate it in flight legally (and if Verizon hadn't
disabled portions of the bluetooth implementation in a misguided
attempt to encourage me to send 25 cent text messages). These
obstacles will be overcome though. My question is... when?

-R