Question Prompt: Time Agents and Time Lords

It’s occurred to me recently (courtesy of family members trying trying to catch up on my DVDs) that Jack Harkness is quite knowledgeable about the Doctor’s business, even soon after the two first met.

That Jack recognized the Dalek ships and had assumed that “they were destroyed” (Bad Wolf) is no surprise–a race as deadly as the Daleks is bound to be recognized sooner or later by the survivors.

But what about earlier in the series, during the events of Boom Town? What is Jack doing with that extrapolator? He’s installing it into the TARDIS… without the Doctor sticking around to help him or give him any instructions, mind you.
Granted, it might have been as simple as telling him where to plug it in–maybe like telling your computer-illiterate relatives where the flash drive goes. Or maybe the TARDIS was guiding him along. Or maybe, just maybe, Jack knew something even then about the workings of a TARDIS.

So my questions and prompts for my readers:

Some of us might remember, if we’ve read the classic novels, that the Doctor has had dealings with the Time Agency before.
But has Jack himself, either as a Time Agent or later as a con-man, had other dealings with the Time Lords? How might such an encounter have gone?

And where else, and when else, have we seen the Doctor allowing his human companions to work on the TARDIS?
Anywhere at all, in the show, the novels, the radio plays, etc.
With or without help, advice, or blatant supervision?
How have those incidents worked out?

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