Is there any value in holding a higher level degree in education (I can’t find how it would help a direct commission, or anything similar)?

last I remember you can't get a commission without a degree. And yes, to go higher up in ranks 05-06 requires Command and Staff College, which graduates you with a Masters degree. Without "Higher" level education the most one could hope for is 04, maybe 05.

I'll comment on the long game. That means depending on what your pursue, your higher level degree may not work as a pedigree item, especially in varied staff corps. So if you want it to hang around longer as worth while on the promotion boards, you'd take a path where it still counts. Make sure you take a look through the various officer "Community Plans" to see all the checkboxes and advanced degree requirements are kosher. Then you have a choice that can be between what you really want to do but the degree doesn't fit and something semi OK with what you have. Do you take the blue pill or the red pill?

Also, there's the Reserve and Guard Tech full time vpcivik service spots wearing the uniform and drilling, I realize you might not want those, given that you teach. Finally, might you also think about other services, possibly USMC, perhaps? Navy or USCG you'd have ti go OCS for those, or possiblyan OIS program (indoc) if you went direct commission. There's also USPHS if you've got any inclination to be in the clinical side at all, in med admin, just a tyhiyght, though u know they scrapped their Reserve program a few yrs ago, just figured I'd mention that. I'm unsure how USAFR might use you, you'd need to ask if you'd have ti go USAF OTS or into an OIS program with them, I know Natl Guard has their own OCS programs, though I don't know about OIS programs for them, I do quite honestly think that direct commission Army cyber program could well be your best hope, you know? Obviously, that'd depend on if you'd want such work, or they'd take what you've got, of course, though you could ask, certainly.