For reasons I don't entirely understand, my solution for this stopped working. I was happily running ViMu on my GoogleTV, and pulling files from my Mac via SMB. This totally stopped working on OS X Mavericks, even when I switched to a WebDAV server. (Symptoms: stream one minute of video then wedge.)

Okay, fine, I've got this TiVo. It should be able to do streaming, right? One cool feature of the new TiVo Roamio is that it supports YouTube casting. That's nice, but not helpful.

What I'm pursuing now: pytivo, hme-for-python, and VidMGR. Years ago, I tried StreamBaby, and it would run for 15 minutes then wedge, and it doesn't look like it's being actively maintained any more.

Anyway, VidMGR is a plugin for the HME thing. When it starts it up, Python complains about "No module named Image", which says I'm supposed to install the Python Image Library. Okay fine, so I did. "Pillow" is supposed to be the preferred way of doing this. The install finished and the relevant files are now in /Library/Python/2.7/site-packages, but yet I still get the same error message.

Very frustrating.

EDIT 1: it seems that if I only configure pyTivo correctly, putting my tivo.com username/password into the pytivo.ini file, then I get some "push" options from the web interface, letting me copy files (not stream them) from my Mac to the TiVo. We won't even start grumbling about how much I don't want to leave passwords sitting around in .ini files on my machine. Maybe I don't actually need VidMGR.

EDIT 2: I spoke too soon. Pushing files to the TiVo is a total fail. The TiVo is clearly receiving the files, but it seems like it's promptly deleting them once they arrive. This seems to be a pyTivo bug, since the logs have every file name listed twice, and the second time it says 0 bytes, 0 Mb/s.

EDIT 3: I tried downloading the newest StreamBaby, which in turn required downloading Java 7 from Oracle. It boots up and runs, but my TiVo can't see it. It's like it's not there at all. Arrgh. I'm now pondering throwing money at this solution and getting a Chromecast, installing Plex, etc.

EDIT 4: Well this is interesting. Apparently pushing from my computer to the TiVo is a loss, but pulling from the TiVo works without issue. The difference? When you push a file, it goes over unmolested but when you pull a file, ffmpeg is running in the background, slamming your CPU, and generating whatever exceptionally restricted flavor of MPEG the TiVo is willing to digest. Also interesting, StreamBaby now appears in the app menu. Launch it and it lists the directories I'm willing to share. Click one of those and it wedges. Sigh.