I would be interested in a different strategy. If you get to the 3th round and beyond and the Oilers aren't excited about drafting anyone in that range then i would trade the pick for 2018 & 2019 picks.
Extra picks next year and beyond will be valuable as you can trade them for immediate help at the deadline without interrupting the inflow of prospects that keeps the whole thing sustainable in the long run.
If you look at Washington for example, they have traded so many picks over the years that they won't be able to sustain their success over the past view few seasons going forward. Especially now since a good portion of that hockey team is moving on to different teams via free agency.
I'd rather have Chia add more bullets in the 2018/2019 chamber going forward than having a few extra lottery ticket selections this year. I also like this strategy because Chia seems to do a good job recruiting NCAA talent to compete for jobs at the NHL & AHL level. I'm not as concerned with finding diamonds in the rough in the later rounds of the draft.
That's pretty smart actually. If we're thinking we're going to be a consistent playoff team. Having additional assets available to move at the deadline would be a considerable bonus.