Bluetooth...Does it connect to Phone & Audio player automatically?

It all depends on the phone and the car BT. Two data points, both using my Android phone with BT:
* In one car, with Alpine W404 and BT, I have to turn BT off and back on just like you (or worse) almost every time. Sometimes I have to unpair and pair again to get it to connect.
* In my new 2011 Prius currently with Blu Logic BT, it works automatically and perfectly 99% of the time. I've only seen the connect fail once in about 100 tries. And it connects both phone and streaming audio.

So... if it is not working for you, first try connecting to the BT in other cars/head units. If it doesn't work anywhere, might be your phone. If it works elsewhere, could be your car BT.

 

We use iPhone 4's and the BT streaming is automatic. We were a bit bummed at not getting Entune buying the 2011 but not an issue since the BT streaming does the same thing.

 

It seems to me that Toyota engineers did not spend a lot of time testing the way we have seen software vendors over the years test hardware and peripherals with their products. I am pretty sure they test all the various iPhones and iPods and perhaps some of the major Droids and MP3 players, but I am only guessing. I can say that most of the time, my iPhone 4 will connect automatically through both the HFP (Phone) and A2DP (Audio) profiles.

I can say they their testing and experience with bluetooth is somewhat restrictive IMHO. Nowhere it is documented (not on their web site nor they various owners manuals) exactly what devices they have tested or will support for either HFP or A2DP (unless I missed it).

So for example, not everything that supports A2DP will play through their speakers or even 'pair' / connect. Take for example a bluetooth enabled Windows Vista laptop. My laptop has absolutely no trouble playing through my A2DP enabled Bose Soundlink speaker. But when I tried to pair the same laptop with the Prius, most of the times the laptop "blue screens" / totally crashes Windows. And when I make it past the bluescreen, Windows tries to connect to the Prius and asks me for Prius specific bluetooth files (which there aren't any). Toyota simply said when I called their national number (since the local dealer service people have no idea how bluetooth works) simply said "we don't support bluetooth laptops".

So the bottom line is from my view, you are pretty much on your own (though the people here will help you if they can) since Toyota will be of little help.

 

Blue Screens -- that sounds like the problem is with your Windows BT implementation.

 

As the Prius is the only bluetooth device this happens to, I would tend to think that they have not totally adhered to or completely implemented A2DP. Hard for me to believe that even though Windows Vista is aged somewhat, that Microsoft would not update Bluetooth support to keep it "evergreen". Bluescreens have historically mean some major incompatibility with the hardhard at the "IRQ" device level.