Yeah, I've done this with my N80. Which surprised me at the time because if the tablets can do this with phones, why not Windows PCs? That's a rhetorical question here...
For some time (over a year) I've used a blue-tooth usb dongle on XP. Dlink.
Two way access to the 770 as well as Sony t670 phones.
Additionally, it came with a sync program that keeps my outlook contacts equal to the phone's book.
Inablilty to contact a phone with the tablet is usually due to the phone carriers' having crippled BT. (Verizon, for example.) They don't include the BT OBEX file service (based on trivial FTP...)
The ability to send files to the phone is well shown in that you don't have to pay for ringtones. This probably is a real reason why the carriers don't want OBEX FT.
I have been absolutely tearing my hair out trying to get files to my N800 from my Mac (OS X 10.4). I followed the advice of baddog and IT WORKS!!! It's all about the OBEX, baby.
So, here's the definitive for getting files FROM a Mac TO your N800 via Bluetooth. (It doesn't work in reverse, but I can cope with that.)
2. In Application Manager, select Browse installable applications. Scroll the list until you find sobexsvr.
3. Install it!
You'll now be able to push files from your Mac to your N800 via Bluetooth (presuming you've set up the N800 as a trusted device on your Mac). I had tried installing sobexsvr before but it just wouldn't do it. This method has worked for me.