Orrin Hatch and Al Gore? Talk about a snoozefest. I don't see why Hatch doesn't win, given that the economy had peaked in March and the two-term alternation rule (except '88) since WWII. Perhaps a Hatch/Dole or dare I say a Hatch/D'Amato ticket?
Hatch would be a weaker candidate than Dubya for sure. For one thing, he doesn't have Dubya's folksiness working in his favor, and for another he can't play the " Washington outsider" card, which was an effective part of Dubya's message. Bush painted Gore as being part of the partisan deadlock that had existed in Washington, Hatch can't do that, being a Senator.
Gore beats Hatch.
Jeb would probably wait for 2004, where he would most likely win. If you want Jeb in 2000 you need to have a POD of him beating Lawton Chiles in the 1994 gubernatorial election.
A Jeb Presidency starting in 2004 is an interesting proposition, one that I haven't seen discussed much at all.
Under a Gore Presidency Iraq doesn't happen (9/11 and Afghanistan still do though), so Jeb doesn't have as much on his plate internationally as second-term Dubya did OTL. I also get the feeling that Jeb would handle Katrina a lot better, since he'd have a lot of experience dealing with Hurricanes from his time as Florida Gov, and under Gore FEMA wouldn't get as messed up. Would Jeb still try to privatise Social Security like Dubya did?
However, if the economy still tanks in 2008 Jeb'll have a tough re-election fight on his hands. No Iraq means no Obama, so I guess Hillary will be the challenger.