Um, I got the Droid for myself and my parents for $50 each (with 2-yr renewal) on Amazon Wireless. For $50, you can't go wrong. Only reason not to pounce on this deal is to wait for the N1 which is supposed to come out late March, but that'll cost you more. Also, take this with a grain of salt, but apparently the Droid's components add up to about $8 more than the N1's.
The Droid's also getting Android 2.1 soon, and if you're okay with rooting the phone (voids warranty), you can overclock the phone to 1 ghz, tether the phone to your laptop (use it as a modem), and other neat things... For the record, I love the Droid, but to be honest it's my first smartphone, so I'm probably not the best judge for comparing these things. The only change I really wish for is the 4 "buttons" along the bottom (back, menu, home, search) to be actual press-type buttons as opposed to touch buttons. If you think you'll need a keyboard, go with the Droid for sure. People rag on its keyboard a lot (for valid reasons), but personally, it just took a little getting used to (write a couple texts and e-mails and you're gravy). Also, having the keyboard is a huge plus for simultaneously typing and viewing in landscape, as a virtual keyboard doesn't need to clog up the screen.
I need to reiterate the fact that it's $50 with 2-yr renewal/contract, which is ****ing cheap as hell for a flagship phone. Hell, the sandisk 16 gb micro sd card it comes with costs $46.75 on amazon.