I did this option in 1995. In hindsight, it has worked out very well for me, though it did shape my choices in ways I was not always happy about at the time.
Significant points that I remember:
MOS choices were very limited. I was a kid who should have had a wide range of MOS choices based on ASVAB scores. In reality, I was offered Stevedore (port operations) and carpenter, neither of which offered college loan repayment. I started to leave the office, and they were able to open a slot for me in a unit as a 92A. This came with a bonus and college loan repayment, so I took it. I really wanted to be a medic though, and should have just left till they found me a job. MOS selection is absolutely a negotiation, especially with Guard/Reserves.
Guard and reserves are two totally different organizations, and the differences can be significant. Guard will have the combat arms and most combat service support roles, whereas the reserves is more logistics and medical. That is not an absolute though.
Make sure you know the commitments, and that lots can change. I did basic in '95 and it went fine. My basic training battery (Ft. Sill) was about 90% guys in the same boat as me, since there is only 1-2 weeks a year they can start the split-op guys and get them back to high school in time.
Also, depending on the unit, the Annual Training can be an impediment to education on time. Most do this during the summer months. Some try to do it in a Spring or Fall which could cost your son a full semester for two weeks of AT. I was fortunate in that I was assigned to a Brigade Headquarters (420th Eng BDE, Bryan, TX). That unit was constantly having operations within the brigade throughout the year. Being a local, I could often come in for a week here or a few days there and get my AT time between semesters, or even get a few extra days and a little extra $$$.
Doing basic training in the summer is hard not to lose weight. Coaches were not happy about seeing me return as a 6'3" 165# Tight End for football.
My recruiter was a world class turd. This did not effect me in many ways, but one was that he could not tell the difference between a 92Y (8 week AIT) and a 92A (12 week AIT), and because of this, I almost missed my first semester at A&M. I graduated AIT on a Monday, was orientations on a Tuesday, and in class the following Monday. I was fortunate that it worked out like it did.
Upon return to A&M, I saw that they had full ride NG scholarships available to guys in my shoes. I applied and was offered one, but really didn't feel like joining the corps the week after finishing AIT, and didn't want to make a commitment that would extend over the next 11 years. (I already owed six, the scholarship would have tacked on five more years). At the time I felt like I had missed my chance to be an officer, but couldn't stomach signing up for more crap.
In hindsight, that worked out great, because I was offered a direct commission upon entry to dental school and a much more valuable scholarship for that. If I had already had the NG commitment, I don't know that I would have taken the Health Professions scholarship. I also learned a lot by doing grunt work. We often had cadets drill with us. I obviously didn't see all they did, but they often seemed to be poorly utilized in a way that I would find very frustrating. Not quite an officer, neither an NCO, no real duties, etc. That was my perspective, I was generally pretty busy at the time.
Your son will be able to collect a limited Montgomery GI bill while enrolled in college and actively drilling. In the late 90's, it was about $200 a month, which was pretty good beer money. However, if he does so, he forfeits the full Active Duty GI bill down the road if he ever goes active. There is also a post 9/11 GI bill now as well, but I don't know how that works with the NG. You also collect drill pay which was between $130-200 a month at the time, as I progressed from E-2 to E-5 over the 4 years.
A VERY significant bonus is that when I did go active, I was 5 years advanced on the pay schedule (only 20 months counts for retirement, but all the time counts for pay). A brand new 2LT makes $2875, a 2LT from the same ROTC class who has 5 years of credit for pay makes $3619, and that difference takes many years to diminish. Even as a middle Major now, the difference is more than $950 a month over my year group peers.
Granted my path has been fairly unique, but it was a very cool opportunity that I'm glad I undertook, both for the lessons I learned and the path it has led me down.