A new Tivo box

If I buy a new Tivo box, is there any way to transfer shows I’ve saved, from the old box? Or if not, is there any way to connect both boxes simultaneously?

Download the shows to your computer using the Tivo Desktop software which you can find on the Tivo website. Then send them back to the new box.

If both are active at the same time on your account, you can transfer wirelessly between TiVo boxes…

But, if your cable company decided to set the copywrite protection flags, you won’t be able to transfer the shows at all (without some serious hacking). Comcast has been known to turn on the flags for everything. Fios (in most areas) doesn’t flag anything.

you can also connect both boxes simultaneously, as you said. As long as your TV has enough inputs or if you buy a switch. I believe even a TiVo with no active plan can still play the recordings that are left on it, last I knew.