Roe should have been overturned 26 years ago in PP vs Casey. And it would have been overturned if Bork had been confirmed in '87. At that time, we still had the 2 original Roe dissenters on the Court (White and Rehnquist). Scalia and Thomas voted to overturn. Bork would have been the 5th vote.
With an Amy Barrett or similar pick replacing Kennedy, Roe could be overturned. Roberts makes me nervous, though. He may not have the guts to drop the hammer. But if Trump wins a 2nd term, Roe's overturn is almost a certainty, as Trump will get to replace at least one more pro-abort justice (RBG). The chances of RBG remaining on the Court past 91 are practically zero... unless she's made a pact with Satan or something (admittedly possible, I know).
“He may not have the guts to drop the hammer (on Roe)”
My preference is for the court to not even re-vist Roe until there are at least 6 justices ready to overturn it. My reasoning goes like this:
1) There are millions on our side who will ‘tune out’ regarding the Supreme Court once Roe is overturned. After all, they only ‘tuned in’ AFTER Roe was decided. We need their help WELL BEYOND Roe - cleaning up the courts is a much bigger victory for us than just Roe, and they will continue to help us, as long as Roe is undecided.
2) A stronger majority than 5-4 will make the ruling overturning Roe, stronger, and the decision will last longer, as it would take 2 or more seat flips to go back to Roe.