It is possible to listen to your unprotected iTunes music on the Tivo, with Tivo Desktop or Galleon, but ITMS protected files won't work. It is technically possible to move specially formatted video files over to the Tivo with Galleon or Tivo Desktop for Windows, too, but it's slow and not exactly easy.
Tivo is supposed to be releasing a new version of Tivo Desktop for Mac which will support downloading and uploading video files.
I dont really know...Is this what you ment by hacking the Tivo and getting iTunes stuff onto it:
Quote from Cnet Asia:
Access your iTunes library through TiVo
Listen to your iTunes music collection via your TiVo with the Home Media Option.
The TiVo Home Media Option (HMO) is included free in the TiVo subscription for the Standalone Series2 TiVo. The HMO brings a whole slew of features, including the ability to schedule recordings over the Web, play MP3s through your television and attached stereo system, display digital photos on your TV, and even stream television shows between Series2 TiVos.
Unfortunately, there is no Home Media Option support for Series1 TiVos or DirecTiVos (a TiVo/DirecTV combination) at the time of this writing.
The latest TiVos that are being sold may already have the HMO installed. It's easy to tell: if you have a Music And Photos menu item on the front TiVo menu, then you're set.
Signing up for the Home Media Option is pretty simple. First, get your networked Series2 TiVo onto your home broadband connection. Any high-speed connection will do just fine.
TiVo recommends two adapters: the WUSB11 Version 2.6 (a Wi-Fi 802.11b adapter) from Linksys's Instant Wireless Series and the USB100TX USB-to-Ethernet (10/100 BaseT) adapter from the Instant Etherfast Series. Users have also reported success using non-TiVo USB-to-Ethernet adapters, such as these:
* Linksys USB100M
* Linksys USB200M
* Netgear FA101
* Netgear FA120
* Belkin F5D5050
* 3Com 3C460B
* Microsoft MN-110
* Hawking UF200
* Hawking UF100
* D-Link DSB-650TX
* D-Link DUB-E100
* Siemens SS1001
* SMC SMC2208
On the Wi-Fi front, the table below lists non-TiVo-recommended USB-to-802.11b adapters and the TiVo service numbers with which they are most likely to work. You can find your service number with a quick trip to TiVo's New Messages & Setup System Information screen. Look for it a couple of lines down from the top.
Initial digits of TiVo service number Alternative USB-to-802.11b adapters
110, 130, 140 Netgear MA101 V.A, D-Link DWL-120 V.A
230, 240 D-Link DWL-120 V.D, Linksys WUSB12, Hawking WU250, Microsoft MN-510
Any Netgear MA101 V.B, D-Link DWL-120 V.E, SMC 2662W V.2, Belkin F5D6050
That said, unless you have one of the unsupported adapters lying about your house, I'd recommend going with one of the recommended ones. Simply plug the adapter into the back of your Series2 (running TiVo OS 4.0 or later) and follow the onscreen directions to get it onto the network.
Point your browser to TiVo's HMO page. You will need the e-mail address and password you provided TiVo when you first activated your TiVo. Don't worry if you've forgotten your password; you can either have a new password assigned and sent to your e-mail address or set up everything again by providing TiVo with your service number. You can find that number on the New Messages & Setup System Information screen.
Once you're signed up and you have your TiVo connected to your home network, you will have to wait for your TiVo to connect to the service to activate itself. If you're a little impatient, you might try forcing your TiVo to connect and download the HMO option right away by having it make its Daily Call: go to the New Messages & Setup System Information screen and select Settings > Phone & Network Setup > Connect to the TiVo service now. If you notice the addition of Music And Photos to your TiVo Central menu, the install worked.
Now that your TiVo is good to go, you need to install software on your Mac or PC. TiVo cannot currently play AAC files, and it can recognize iTunes playlists only on the Mac. Follow the included instructions for turning on MP3 sharing on your Mac or PC, and you'll be able to listen to music on your TiVo in no time.

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