Audio
I've bought an S9 to use with my phone just as well, mostly to use while mowing lawn. The audio is nothing special, but it pairs and connects easily to my phone, and give me adequate stereo fidelity with no hassles or issues. Pairing, changing tracks, answering the phone while listening to podcasts is simple and obvious. The buttons are way too touchy, but other than that, it works.
I also bought a Motorola T305 also, hoping to use it to play podcasts while driving on long trips. The concept is great, but unfortunately is simply isn't loud enough to overcome the road noise on my vehicles. Close, but not quite. My cars apparently aren't particularly quite. A T505 that outputs audio via your FM radio might be ticket.
On the computer side of the equation, I've got a handful of devices that support BT to some degree The Mac is pretty close to having decent BT audio. It doesn't automatically use the headset or headphones, unless I use a 'Use Headphones' menu, but once that is done, it uses the headphones when they are on, and switches back to on board audio when they are not.
File Transfer.
Apple still treats Bluetooth file transfers like a 1980's FTP session. Of course you don't have to use a command line, but the GUI that they present is only slightly better. Apple's designers are are still thinking that you connect to a BT device, browse through the device file system, and transfer files to & from the remote BT device as you would a with 20 year old FTP session. Drag and drop works, but drag and drop is really still treated as a file transfer, not as a seamless part of the native file system.
Vista tries to treat a Bluetooth file transfer as a network attached drive. It builds folders in explorer for the various devices and lets be drag, drop, rename, etc. It doesn't seem very robust though. I can easily break it by playing around with my BT adapter (unplugging it and re-plugging it). It still thinks I'm connected, even why my phone is off, and generates useless error messages when I try to access the Bluetooth file system. It doesn't handle error conditions very well.
The same operation on my N800 is much different. The N800 sees BT devices as a mountable file system. Any paired and in-range BT file devices show up simply as mounted subdirectory that the file manger sees just like any other part of the N800's file system. That is one of the best parts of using the N800. If I see and interesting podcast, I save it to the N800, then drag & drop it over to my mp3 phone using the N800 file manager. It's not a separate application just for moving files around with Bluetooth, it is a Bluetooth file system seamlessly integrated in to the device. No tethering, no wires, no iTunes.
Nokia really did a great job integrating dialup networking with the N800's Bluetooth stack. If I want to use my phone for internet access from my N800, I run a simple wizard once, then pick the phone from the wireless connection menu. As far as the N800 cares, GPRS, Edge, 3G HSDPA, and B/G WiFi are all the same. And with 3G, my internet connection speed is around 1mbps. Very well done.
I played around with using Bluetooth DUN from both Vista and XP. With the proper software, it is pretty straightforward and simple. Half-way through editing this post from m Vista machine, I launched Motorola Phone Tools, clicked on the Internet button, and switched my network connection from Wifi to ATT 3G and finished the post. Pretty neat and easy.
Using Bluetooth for Internet access from the Mac wasn't anything like seamless or painless. Considering that the phone and the Mac are already paired, I obviously should be able to select my phone from the same pulldown as I select Wifi networks, like the N800, but following that thread leads to a dead end. Network preferences shows my phone, not connected (actually it shows a whole bunch of phones, because apparently it never occurred to an Apple engineer that I might want to delete a phone from network preferences......) and leaves me with no way of connecting . In any case, there doesn't seem to be a logical menu or button that connects my phone to the Mac via BT, in spite of trying multiple dialogues, buttons, pulldowns & whatever.
Bluetooth Preferences shows the phone, not connected, and leaves me with no combination of splat-ctrl-fn-alt anything that will light up BT to the phone. Using the BT browse device menu will let me connect to the phone via OBEX, but that doesn't light up the DUN connection. Network preferences shows all kinds of borked dialup connections, and does strange things when I try to configure them with Cingular's config.
In any case, randomly clicking around eventually gets it to work, somehow, but some unknown combination of magic clicks & incantations.
The Mac to DUN connection via a Bluetooth phone is a pain, simply because the UI isn't simple or obvious.