re: Can States Invoke the 10th Amendment to override a Presidential EO such as the Keystone

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No. The Commerce Clause and court interpretation of same has effectively neutered states. Anything that deals with interstate commerce is federal. There was a case that I think went to SCOTUS long ago that said states with snow/ice problems couldn’t even require use of certain mudflaps on trucks using their roads bc it affected interstate commerce.

I am sure there are a number of reasons the states are fricked, but this is one of them.

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I'm not sure what the EO says and the specific situation of the pipeline, but not sure what you said really has any relevance.

There are limits to the ability of the federal government to regulate things that impact interstate commerce. I mean in theory, if you were to produce farts than can the federal government control your food intake to limit said gases which could in theory impact interstate commerce.

The mud flap case is a specific instance of a state trying to control interstate commerce to a degree which was unconstitutional. Those same trucks are required to have brake lights.

I would say the amount of the impact of interstate commerce would be a factor in a general sense, and I would imagine without looking at the regulations that a large pipeline like that is regulated.

The issue here is probably why was the EO done and was it in violation of law i.e. "arbitrary, capricious, an abuse of discretion, or otherwise not in accordance with law".

I am not saying the federal government can't regulate the pipeline, but the devil is in the details. I would assume the investors could have additional claims against the federal government but I don't know enough about those details to even know where to begin.

In this case, what the OP is suggesting is the States by pass any restrictions by the federal government, not impose new restrictions.

https://www.scotusblog.com/2014/06/opinion-analysis-epa-mostly-wins-but-with-criticism/

This is an EPA case where the EPA actually won most of what they wanted but the USSC started sending shots across the bow.