As for the comment about not being a generalist/not being buried in PPTs procurement... results certainly vary by airframe, track, and unit.
Sounds like someone went TACOPS (possibly Safety, but generally not as dire)? I always felt sorry for my fellows that got pulled up to the Bn S3 shop.
As for the direct commission, no. I went CW3 to CPT in late 2010, but mine was different as I already had 9 years previous as an RLO. But obviously there is precedent as you posted. If no one helps you out/is familiar, suggest you do one of two things--hit up that captain in the article on pointers...and if he'd still do it (find him on global) or query HRC-Avn (generally the "special actions" officer on the branch webpage).
I will say O3E is good money when up in the 15-16 year area, but if CW4 is likely / possible, you'll make more in retirement than a MAJ if you are staying a little beyond 20 (O-4s only get annual COLA above 18, no TIS increase).