I don't know that this will help everyone, but I have a nuvi 285WT that was running v4.8 and would reboot right after connecting to my iPhone (2.2.1). I came home, plugged the GPS in, did the web updater thing, and found an update to 5.0. After doing this update (and the extras that applied to me or the unit) I paired with my iPhone again...and it worked! Phone book and all was there and working fine. I turned the GPS off and on again to make sure I wasn't dreaming and it hasn't had any more issues.
So for those of you with a nuvi 200-series running < v5.0 I'd try upgrading to 5.0 and make sure you select any other firmware updates that apply. Hopefully this will help some of you out. I don't know what the difference between the 265W and 285W are, Garmin doesn't even list the 285W on their site, but updating worked for me.