Wakie,all good takes. I think your timeline is absolutely plausible. And I like the bet in Hillary going to work in DC. Didnt think of that. And
Here's some factors I thought of. Clinton in the 70s and early 80s was a liberal. OTL he lost the Arkansas governorship once because of his taxing ways. He became more moderate when he re-acquired the governorship. It seems likely he would rack up a liberal voting record that would be used against him. He could probably work around it, but it would be a stumbling block......and one not as easily hidden in a fairly obscure state like Arkansas.
You noted Clinton would probably leave Congress after a term or two and go into state executive branch politics. A reasonable conjecture. But I will say he would have to to make your timeline work. First, hes going to hit the ground in Arkansas a liberal (at this time, Democrat Congressmen made their careers by voting hyper-liberal and running campaigns not on voting record but on how many programs and work projects they brought to the state). That puts the gubernatorial loss for being a "Tie Dye Hippie" sort closer to the 1992 election cycle. Not a good thing. And I dont think running for the president out of Congress is good given that few presidents have come with a legislative pedigree especially by the 1970s.