I Must Be Misunderstanding The Long Term Plan

The oilers will be fantastic when the salary cap reaches $94M.

By the time the salary cap reaches $94M, the Oilers will have spent $120M

Ken Holland:

https://i.imgflip.com/5j3hfc.jpg
Ken Holland is the new Jim Benning

Overall you have a point. However:

1. The Oilers have 4, most likely 5, ELC contracts that they're betting the farm on next season. The group of Broberg, Holloway, Konovalov, Lavoie, and Samorukov are probably going to be looked at to help drive the bus on next year's squad at massive savings. The difference alone in running Holloway, Konovalov, and Samorukov over your UFA placeholders is $8M with room for bonuses.

2. The second contracts for Bouchard, McLeod, and one of Puljujarvi/Yamamoto probably come in less than your placeholders do. Bouchard is maybe bridged over two years at less than $2M, McLeod for around $1.5M, and Puljujarvi and/or Yamamoto probably top out at $3.5. There inlies another $3M in realized savings worst case scenario.

3. Moving Kassian isn't impossible

All things considered and even ignoring option 3, were at the point where a projected $1M cap increase, press box deals coming in cheaper, and cheaper 4th line deals probably put the Oilers under the cap even if it's only by a small margin.

Granted I don't believe the Oilers will try to find a taker for even a 50%-retained Kassian and that we need to seriously expect a Puljujarvi trade. The organization is clearly high on Konovalov, Skinner, or both, and Holland is super high on his own drafted prospects.

ELC deals appear to be the only way forward in the meantime and it's not going to make next season's cap situation tricky, but rather 2, 3, and 4 seasons out.