Enlist or apply for OCS with a master’s degree?

One thing to consider is the age disparity between you and your peers.
3 years is not a huge difference between you and the rest of the LTs. 7 years between you and the rest of the PVTS is. Even if you are guaranteed SPC out of boot camp, you have an uphill climb until you are granted similar responsibilities to that which you are already used to. You are already an adult, living in an adult world, managing yourself like an adult. This is not to imply being a junior enlisted will be a step back, but it is definitely not a step up.

It really depends on what you want to do. You have virtually no control over your branch when you commission. If you enlist, you can pick your job including MI. The lifestyles are also quite different. I had a bachelors degree but I enlisted first because I was offered a significant enlistment bonus in 2002 to be an Arabic cryptolinguist for MI and the value of that bonus over 5 years in conjunction with my pay was higher than LT pay and the job was pretty cool. It eventually got to the point in my career where I knew I would stay in for 20 and had to decide if I would stay enlisted, go warrant, or go OCS. My personal decision was based on a lot of factors. I will say that as someone who commissioned as a SSG, there is not one life that is better than another. There are things I really miss about being an NCO and there are things I’m glad to have experienced as an officer. So truly, the answer is really about what you want to do.

I used the GI Bill to get a college degree and then go ocs but kids came along and decided to be a cop! I'd say ocs!