The whole purpose of your argument was that Roosevelt only felt "safe" in using Executive Orders because he wouldn't have to face another election.
But the exact opposite was true. Roosevelt felt that he could get by with the Executive Orders because he felt the people would support him over Congress.
And he was mostly right. Most of the issues he advanced with Executive Orders were extremely popular with the people which isn't surprising given that Roosevelt won by a mind-blowing 18.8% spread in 1904. His issues were so popular, that Taft (his hand picked successor) easily won over William Jennings Bryan in 1908 on the platform that he would continue Roosevelt's policies.
Roosevelt used Executive Orders far more than any President who preceded him, but he did so because he felt he had the public's support, not because he knew he wouldn't have to face them again.
"after he would have no longer been up for re-election - a classic scheme that progressives do."
Even if Roosevelt's policies would've been less popular, he would've done them anyways. Progressives always try to do things when people aren't looking, or change the label, or something else that in effect re-packages the content. Do it on a friday evening, or on the day before/day after Thanksgiving day. Bring in friendly journalists so that they report it a certain way. Any/all of these are fair game and they're not new. They're just more common now.
For progressives, progressivism is always first. Nothing comes before the faith.
As for "safe", yes, I did have a little bit of that in mind, but mostly I'm looking at his ideology. That, and TR was a bold guy. He wouldn't have thought much about "safe", so I wouldn't factor that in too much. This is a question of ideology. Progressive ideology. You do know that TR promised not to run for a third term, correct?
Who knows if TR could have won his third term consecutively - that's a lesser of a question than is why did he make the promise not to in the first place? 100 years ago, the progressives didn't have what they have today - most Americans still knew about the Founders, the actual truth, there hadn't been widespread disinformation at the time. It took their historians and universities a century to put all of this propaganda in place.
His making that specific promise was an acknowledgment of what the people had expected up until that time from a president.
So he boxed himself in(boxed himself out of?) from there ever being any electoral accountability? So what? The end result is the same. Once he won his second term and that was going to be the end of it? It was pedal to the metal, balls to the wall. He's the man of action, he's going to do anything that he wants. That Constitution is not going to stand in TR's way. It's going to be all statism, all Constitution shredding, all the time. And it was. The end result is the same.