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IMO the smoothest path is EyeTV. I've had EyeTV for many years, but never really relied on it until now. I cut the cord a few years ago, but at the time TiVo was a better option with better features; and it was much cheaper $10 a month vs. $20 today. I only record OTA and I started to feel that paying a monthly/yearly fee for "free" TV doesn't make a lot of sense. So recently I ditched the TiVo and switched completely to EyeTV.
A few words of wisdom I'd impart would be to invest in at least one HDHomeRun Dual tuners ($89 w/o ETV bundled), I recently purchased a second one as it allows more flexibility in scheduling and watching live tv while recording up to 3 programs at the same time.
For automatically encoding to an iTunes compatible file, an Elgato Turbo.264 HD definitely helps speed up the process.
All in, you'd probably still be within the TiVo price range for the first year.
One more thing, the only semi-reliable way I've found to get TiVo files to the Mac is with iTiVo, a java based app that does the job, but it's a very long and tedious process. If you like being frustrated, than that's an option as well
Anyway, I hope this helps!
Thanks!
mac.jedi