I think there is a lot to discuss here.

Do I just get one shot or can I keep trying until I get it right? Basically anything that reduces Republican power in the US is probably a win overall.

So, the Republican shift toward the far right was already in full swing by the 2000s. You’d need to go back to at least Reagan to head that off. Trickle down economics, Two Santas, etc. was already decades in the making. My dad had already been fully brainwashed by talk radio in the 90s. But on the flip side, the Democratic establishment has made it painfully clear even to this day that their only priority has always been to maintain the status quo for the privileged NIMBY class. The Republican party didn’t need to do anything to keep unaffordability rising, they all want to maintain the housing market bubble to protect the wealth of boomers.

We make it so Reagan still runs but doesn't win presidency, ever, until he dies. We make sure Bill Clinton doesn't do that incident with Monica that got him impeached so he can still have some goodwill with the people enough to make them think we want the current path he paved to continue.

Clinton mostly became president by embracing Reaganism, so he didn’t really pave the path and it did continue