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I'm wondering where Livia goes between their meetings.

Or just as important, why she gets to hang out with Dan. Either she's learned to control it or she's on a long-term mission to save him.

And how come the brother hasn't put two and two together yet with the $20?

He encountered the $20 a number of years before the bill was redesigned. Either he threw it out, gave it back to the cabbie, or filed it away as evidence; either way he almost certainly forgot about it, and when the bill was redesigned I doubt he would have recognized it. At most he would have thought, heh, if I remember correctly that bill I confiscated a few years ago looked a lot like this new one. But the last thing he would have guessed was that it was brought from the future by his brother.

Buy a lot of stock in Google or whatever.

You mean "FinderSpyder".
He could open a savings account as "early" as possible (under a fake name of course so they wouldn't send statements to his past self), deposit as much as he can, and cash it out in the present. And then whenever he's anywhere in the timeline at a point after the account is open, he puts all that money back into the account, a strategy which would either give him an infinite supply of present-day money or blow up the universe, depending on the show's time-travel rules.

Notes and nitpicks:
- I wonder how far he can go back. Sam Beckett was limited to his own lifetime; are there similar boundaries here? Or could he wake up in the wilderness and save someone during the gold rush?
- At one point he prints a list of earthquake victims. The next time he jumps he tries to interfere enough to save his boss's sister or at least affect the death toll in some way. When he gets back to the present, he checks the website against his printout, and they're the same. He concludes he didn't make any changes. But if he did make changes, wouldn't the printout change? Or is it immune because he carried it with him? (I guess it would have to be according to the show's rules: he's remembered events the way they occurred before he changed them, when technically his memory should have changed as well)
- The present-day events seemed to occur around the actual airdate of the episode, 10/8/07, because Dan mentions the 18th anniversary of the earthquake is "next week". But a few scenes previously some characters were talking about a baseball game they had watched. Unless his intervening jump made him go missing for a week, it would mean that the Giants were playing in October, and therefore in the playoffs. The Giants had a lousy year, so unless the episode was filmed in or before April, it should have been obvious for most of the season that the Giants were not going to be making the playoffs. Of course, they could have just been talking about a playoff game featuring other teams.

This is a terrific show that really seems to know what it's doing. I have no hope for its survival but I'm sticking with it just the same.