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Part of the problem with this is legal case is that with a few (largely nuclear-related) exceptions, all classification guidance exists in the form of Executive Orders. The current guidance is EO 13526 from 2010, but that revoked and replaced a whole list of orders from previous administrations dating back to Harry Truman. So if the question is "could Trump have declassified this?", he could have declassified (almost) everything by mere a executive order revoking 13526 without replacement. In addition, the EO 13526 explicitly designates the President (and Vice President) as a "classification authority" able to determine classification.
But what constitutes an executive order? In general, the separate powers of the US federal government are given broad leeway to determine their own rules and procedures (see Noel Canning, which found that the Senate is in recess only when it declares itself as such). I can't see any reasonable court deciding that failing to write on official White House stationary invalidates an executive order. There might be an argument that the President wasn't faithfully executing the laws as passed by Congress, but the Legislature has its own means (impeachment) for enforcing that.
If the contention is that the illegal acts happened after he was president, that's a potential case, but I think it still faces a fairly high bar to show that keeping the documents wasn't justified by actions taken as president: that would require a court to take significant leeway in interpreting how the executive ran its operations. A precedent of "just because a President [claims to have] issued verbal instructions to do things that are lawful except for violating prior executive orders doesn't prevent your prosecution for violating those prior orders" would be terrible.
Does an elected President (in particular, one with no prior service) even have to sign SF 312? That NDA is the vehicle through which most criminal charges for mishandling classified information flow, and without it it's unclear that any charges could stick to a non-signatory. That's why the powers that be can't charge the journalists at The Washington Post who published the Snowden leaks.
Now, the fact that classification is almost entirely due to Executive fiat is, I would agree, a terrible arrangement, and it would make quite a bit of sense to codify (much of) the existing ruleset through an act of Congress. But, in its great wisdom, Congress hasn't decided that doing so is worth its effort. Ultimately, I'm not a fan of Trump, but this really seems like a politicized effort to bring historically unprecedented charges.
My brief interactions with the government bureaucracy surrounding classified documents has made think of the classification process as infectious. I might have some details wrong, but I feel like I understand the broad strokes.
Anything and anyone around big secrets tend to become secret as well. And eventually things must either end in everything being secret or nothing being secret.
Lets illustrate the process:
There is a nuclear missile silo out in the middle of Kansas. It is secret. It needs to stay secret in case of a nuclear exchange. But you need soldiers (who need to be cleared) to man the silo. Their purpose for being out in Kansas now must be made secret. You need technicians who might need to occasionally check up on the silo. These people need to be cleared to make sure they can handle the secrets, also their reason for visiting Kansas needs to be made secret. The construction of the silo, secret. The replacement parts bought for it, secret. The logistics officer that makes sure people and parts are sent out there, he needs to be cleared, and what he works on needs to be secret so no one can target him to figure out the silo locations. Every piece of the supply chain that touches this missile silo needs to be secret, and to be handled by people who are cleared for that secret information.
There is of course not one missile silo, or one single thing that needs to be kept secret. There are many things that justifiably need to be kept secret. But the process of keeping those secrets involves closing down all the avenues for figuring out the secret from second hand sources. And maybe even third hand sources. Or accidentally 4th, 5th, and 6th hand sources. Because access to classified documents is a "need to know basis" no one in the chain is necessarily certain where they are in the chain.
This is why secrecy and classification is infectious. Right now if you work at all with certain government agencies, like any branch of the military, the CIA, FBI, etc then you will almost certainly have to get a top secret clearance. And all you might ever do is touch the most boring and mundane documents and projects. The system of secrets is illegible even to itself.
It sometimes works this way, but there are certainly cases where specific facts can remain classified in isolation on systems that are acknowledged. The DoD likes to claim top speeds "in excess of" a public value, while the actual numbers are much more closely guarded, and they presumably avoid exceeding the claimed value outside of controlled conditions. Your missile silos in North Dakota are part of Minot Air Force Base, which even has a public web site, but I doubt the silo coordinates are on it. I can only assume that completely secret programs are particularly expensive and avoided when possible.
Although I'll agree that your concern is reasonable and there are plenty of folks worried about overclassification, even within the government.
The need to hold the clearance doesn't imply constantly working with such material. I've talked to folks with TS clearances who have offices with windows: sometimes it's a small fraction of the job in a separate space. But having a standing clearance makes it easier to have certain discussions on short notice (and, as someone once told me, "prevents paperwork when people make mistakes").
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