The Series 1 DTivo's will never be upgraded and are running 3.0.1c2 (or something like that). Unlikely DirecTV will actively disenfranchise all Series 1 users any time soon.
The next step for hacking on a DTivo is 7.x, not for TivoToGo, but for the Tivo SDK thing so we can run those applications (which might be cool). Not a huge driving force though.
Tivo since '99, DirecTV since '96, Comcast since '06, FiOS TV '07!
3 x S2 DT
2 x S3 w/ 2xCCs and 1.5TB each
2 x TivoHD w/ 2xCCs and 1TB each
Sony Black Pearl on 110" Stewart FHG3