By way of draft pick values alone, not enough coming back to Edmonton in the Philadelphia trade. Any trade for Edmonton's pick - mathematically - that involves a pick later than #19, would essentially require a supplementary late first in order to be considered a fair deal. The only other workaround to that is through quantity or by doing Edmonton a cap favour.
For the mathematical elements of this post, I'll be referring to:
https://bluebulletreport.com/2019/06/05/2018-19-draft-model-update-part-iii-blue-bullet-draft-pick-value-chart/
The difference in value between Edmonton's pick (#14, valued at 21.1) and the two Philadelphia picks (assuming #28 and #59, values of 10.7 and 3.6) is just shy of pick #33, which carries a value of 8.0.
In the event Edmonton genuinely is considering trading down, this trade should be considered a loss. That is significant value left on the table, and I couldn't pull the trigger on that trade without a name like Bobby Brink being added to the deal, given he was picked last year in proximity to the 33rd pick (assuming Edmonton in turn, adds a touch on their end to compensate for Brink's higher D+1 value). I'd think it would be reasonable for Flyers fans to turn their nose down at that deal. That's a lot to table for the #14 pick, and I don't think there's a name in that range the Flyers would be that desperate to jump for.
I think Holland's intent behind trading the #14 pick back into the later stages of the first round is built around the idea of acquiring an NHL-ready player in the deal as well. Either a piece they can immediately add to the top-nine forwards or a goaltender ready to platoon with Koskinen. I don't think the endgame here is strictly draft picks, and I don't think there exists a dance partner for the Oilers if their motive is magic beans in exchange for #14.
I think Athanasiou's value is closer to a 3rd and a 5th. Mathematically, it's below the 50%-value he was acquired for and Holland tipped too much of his hand. Andreas is immediately a buy-low-win-high candidate and expecting even 50% value is a stretch. I think you're too high on the returns for Chiasson and Russell as well. The flat cap and how it's going to affect teams during its tenure cannot be understated.
I fail to understand the rationale behind that New York trade.