Should I stay enlisted or go for a commission?

There’s pros and cons to both Officer and Enlisted. Personally, I don’t think I could pull it off as an Officer. The subjectivity of the OER would drive me nuts. I applaud the Officers for their patience, especially at the JO levels. Some of the members are extremely intelligent and diligent in their duties, yet a lot will be passed over. Statistically only 17% of military members make it to the retirement years (Officer and Enlisted combined). That number will most likely decrease with the new retirement system that came online 1 JAN 2018, leaving vacancies or gaps (a.k.a. opportunities). Nevertheless, Officers are more heavily recruited when they leave the military.
The money dramatically increases with the number of years served so at the Senior Enlisted rank it isn’t too bad at all. It’ll just take you a bit longer as enlisted to get to the same dollar amount as the JO.
Want more statistics? Ok, roughly 2.5% of the military is allowed by congress to reach the E-8 level. Only 1% is allowed to serve at the E-9 level. It’s a question of chance really. What are your chances of making it to the O-5 level (where the money really gets good) without getting passed over twice versus the Senior Enlisted level? New programs are always coming online and other programs are getting cut, personnel increases / decreases, Reduction in Forces (RIFs), High Year Tenure (HYT). It’s hard thing to nail down and make your career projections. It makes a difference which career field you have chosen. The bottom-line is to go in the direction where you’d have the least amount of regret later. Either way, I wish you the best of luck to you on your decision.

Go for the commission.

Go Warrant and become a pilot.