The last EO came out too late to make a big dent. This one has at least 4 years to work.

How would this work, though?

Executive orders aren't laws. They're orders to the government to take certain actions, or do them in certain ways. They are the President formalizing his instructions to federal employees.

So an EO can order the Department of Health and Human Services to do (or not do) a certain thing. But an EO can't order a hospital or doctor to do a certain thing.

In order to require a private party to do (or not do) something, you need to have a statute. The President doesn't have any legislative power - he can only execute the laws passed by Congress.

So there's already a statute that requires price disclosure by hospitals that exceed a certain size, and that statute has already been implemented by regulation. CMS fines hospitals that don't comply with it:

cms.gov - Enforcement actions

So when Trump issued his first EO back in June 2019, it was a direction to HHS to come up with whatever regulations it could issue consistent with existing law to increase price transparency. I couldn't find, though, that they ever actually drafted any. I don't know whether that's because they got busy with other stuff (COVID-19 kind of reprioritized everything in the health care agencies)....but it may simply be that there isn't any statutory authority to require private parties to disclose prices beyond that already in the regulations.

Absent a grant of statutory authority that's previously gone unused, this EO won't have much effect at all. I suppose it's possible that there's something out there, but I think it's far more likely that this EO won't have any greater impact than the prior one.