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I've had my TiVo since Y2K and I can't imagine going back to TV without it. Every time I have to use a non-TiVo TV it just feels broken.
I still have the original Series1 TiVo I bought back then, though it has been upgraded several times since (bigger disk, CacheCard, etc). I've so far resisted the urge to buy an HDTV since I would need to get a TiVoHD to go with it and, to this date, the TiVoHD is a much less hacker-friendly box. Oh, and I missed the deadline to tranfer my lifetime subscription. D'oh.
I recently purchased a Zenith DTT900 (aka Insignia NS-DXA1) using a $40 DTV coupon to see what HDTV reception was like in my area. I was able to pickup a number of stations using a simple in-door antenna (rabitt ears and a UHF loop). However, there's no TiVo support for DTV converter boxes. Thus began my weekend project of hacking my TiVo to be able to drive the DTV converter. Hopefully, this info will be useful to others who want to control their own DTV converter boxes.
My next project will probably be to try a roof-mounted antenna and see how many stations I can receive. Maybe then I can justify buyin an HDTV ;-)