Apple iPhone 3G
The 3G ($199 to $299 list) is one of the best handheld computers ever. True GPS, media capabilities, and hundreds of programs through the App Store give it an edge. The phone isn't the greatest, but it's a big improvement. By now Apple should have fixed the bugs that marred some of the initial units.
(as of 12/31/1999 8:00 PM EST - details