Here's a few starting numbers.
The standards (PC Magazine) for 801g indicate 120M line of sight outdoors. I have read articles about people getting reception at 1000 feet using some of the newer MIMO technolgy under perfect conditions (no standard yet on 802n).
I believe a mile is roughly 5,280 feet so you would need to use several "extensions" which are like repeating access points. I believe the greatest difficulty using "off the shelf" technology would be finding 7 or 8 places along the route to install the repeaters. Then again, you have to have a wireless router hooked to your office network to start the whole thing off.
For $2,000, your friend must be talking about an "industrial solution" similar to what some of the Amercan cities are starting to install (very large broadcast dishes basically).