Get the officer recruiter to nail down the date he can start OTS. He knows who to contact for a realistic date - give or take one rotation. He knows many other officer recruiters and the least he can do is call a few and ask how it looks. He also knows the name of the CMSgt (Chief Master Sergeant) that is the key person in charge of OTS scheduling. That CmSgt knows the facts like he knows what time the NCO Club closes. He works for an officer. But he runs the show. Without saying what the Chief would or should do, he can do what needs to be done.
At any one time, there are two classes at OTS - the uppers and the lowers. So every 6 weeks =one rotation - a new class of lowers arrives, the lower class goes upper and the upper gets the brown bar. 12 weeks total.
You probably knew that. Point being there is no reason they can't nail it down give or take a rotation. The rotations all have dates, each class size is set and they know the number of applicants in the pipeline.. Also, he needs to get everything done that need's doing - AFOQT for example.
OTS takes enlisted types, but there is no guarantee. Ask the officer recruiter if the age limit applies to enlisted as well.
If he can get intelligence work, then go for it. Given his education, he'll be a lot happier. And don't sell Army OCS short.