SO. FUCKING. AWESOME.
I got it all working. I now have an Android Activity (GarageDoorActivity) which interacts with an Android Service I wrote (InRangeService), letting me start and stop the service's wifi scanning task. The service gets the system WifiManager, holds a WifiLock to keep the radio active, and then does a Wifi scan every couple seconds, looking for my house.
When my house is in range, it does the magic HTTP request to my garage door opener's webserver (HMAC-signed timestamped URL, for non-replayability/forgeability if sniffed) and my garage door opens. Complete with a bunch of fun Toast notifications (like Growl) and Android Notifications (both persistent ongoing notifications for background scanning, and one-time notifications for things like the garage door actually opening).
I just threw on some shoes and hopped on my motorcycle to do a test lap around the neighborhood. When I got to the corner, I pulled up the activity and press "Start" (aka "Going home now"). A lady on the corner saw me playing with my phone on my motorcycle and said, "The reception's not so good up here." I thanked her, not wanting to explain what I was actually doing.
I then finished the lap around the block and the garage door started opening a few houses away. By the time I pulled up, I could already back the bike into the garage. HELL YES.
Update 2008-11-16: The source code is now available.