Based on the language in the executive order:

"the entry into the United States of aliens as nonimmigrants to perform services in a specialty occupation under section 101(a)(15)(H)(i)(b) of the INA, 8 U.S.C. 1101(a)(15)(H)(i)(b), is restricted, except for those aliens whose petitions are accompanied or supplemented by a payment of $100,000"

It sounds like it applies every time you leave and enter, provided you are a nonimmigrant alien on H1B (which they all are).

There are a bunch of H1Bs working as teachers in my medium sized midwestern city, making around $50k. Then there are a bunch in the healthcare sectors making from $50k to $500k. I actually feel like they are legitimate reasons they are there, very difficult to get good healthcare workers in the midwest since no one good wants to go there.

There is a big problem with ethnic nepotism and ghost jobs. I have been struggling to get younger people in my network hired anywhere despite solid resumes. Continuing to issue H1Bs in the current job market was bananas.

It's a severely under-reported aspect of this issue that a troubling amount of times, the issue isn't that Americans want too much money or just don't want to work, the issue is there are no Americans qualified to do the work you need to do who are looking for a job.

The Hyundai factory exposed this. The VISA'd employees (or non-VISA'd? I don't remember the details offhand) were only there in the first place overseeing the project because they literally could not find anyone qualified to do the fucking job in Georgia.

It is not, and don't be. If you were not previously qualified you won't suddenly be. The job will simply migrate overseas.