Ovechkin has his money and a Cup. He now seems fixated on 99's record. Would he take slightly less than market value to play with a guy like McDavid? That (probably) gives him a better chance of breaking it in less games than Gretzky, which would make the achievement all the more special.
Say he decides to take 3 years/30 million next summer. The Oilers could buy out a guy like Neal and trim up the rest of their roster to make it work while still fielding a competitive roster. From there, he'd need to score 895 in less than 335 games (which works out almost exactly to 4 82-game seasons). That's an average of 46 goals a season. He probably reaches that in 2020-21 without much trouble, but it's ages 38-40 where a combo of age, wear and tear, and any more pandemic-related issues may hurt him the most.
That's where McDavid comes in- join those two together at the hip and I think Ovechkin easily gets to 900, probably sometime around the halfway mark of the 2024 season. He can then either elect to retire at the end of his Oilers deal or head back to Washington on one last contract and take a shot at 1,000 while he's at it.
It's a fun storyline to think about- Gretzky in the stands to watch Ovechkin chasing 895 as an Oiler. Would love to see it.