The Oilers are kind of in between a rock and a hard place though. They need to upgrade significantly in two spaces - goal, and 2nd pair RD. Both spots are difficult to upgrade, and they have, at most, enough to upgrade in one on those spots with a guaranteed upgrade. Could they go out and shop for a 5M goalie at the deadline to help shore things up? Absolutely they could. But does that help them now, when their backup is outplaying the starter, and the backup would be in the AHL on most teams? If they get Blackwood, they are getting a goalie who has a lot of the tools needed to be successful, despite not necessarily showing that consistently in the past. It's a bit of a gamble, but it could be worth it if it does work.
If the Oilers were to do this, I would almost rather work something around Skinner for Blackwood, rather than Pickard for Blackwood. I don't want two goalies with a history of consistency issues.