I am, generally speaking, not of a patient mindset when it comes to the Oilers. But this is their scenario next summer:
McDavid, Draisaitl, RNH, Chiasson, Khaira, Lucic signed at F. Klefbom, Larsson, Russell signed at D. Koskinen signed at G. 24.9M in cap space against a flat salary cap. Russell has 1 year remaining, is due a 15 team trade list, makes 1.5M in real money. Lucic is due 9M over 3YRS in real dollars. They'll know about Koskinen, one way or the other. The buyout is 2.5/1.3/1.3/1.3 if need be and if it doesn't need to happen, chances are they feel better about him. Even so, the three remaining problem contracts are night and day easier to manage.
They have the flexibility to almost entirely remake their team around their core based on information this year. You have to think a portion of the cluster that includes Benson, Marody, Yamamoto, McLeod, Jones, Bear, Persson, Bouchard, Lagesson and Samorukov will make up a cost controlled part of the roster w/ one year and two training camps between now and then to earn spots. And the foreknowledge that they could expect an 8-10M cap jump in 2021 to mitigate the risk on buying high and signing pricy contracts in 2020.
As for this year, I think they need to add ~7 wins. Lots of lanes for that happen. A team save percentage closer to Vancouver's .905 versus the Oilers .896 would be huge. 30 goals on the LW from the 2, 3 and 4 lines instead of the 9 they actually got would be huge. A PK in the 80 percent range, still not very good, would be over a quarter of the Oilers goal differential hole by itself. Marginal upgrades in several key areas that are realistic enough could swing that by themselves.