Thinking about trying to become an officer for career longevity. Do you all think I should maybe become an E5 or E6 before commissioning ?

Honest to god truth is become an officer as soon as possible if that is your true goal. I was a PFC upon acceptance to OCS, but a SGT by the time I got a class date. With six years between promotions you'll have plenty of time to mature as an officer. Every individual is different and it is impossible to prove that a prior service e-6 is any better than an e-5. However, with that said statistically so many leave at or around 20 years it doesn't matter what you say now, but you career is limited in duration. Don't spin your wheels!

You should become an officer as soon as possible and begin your development as an officer rather than continue to develop as a SGT. Think of it this way. The way you develop as an officer leader, in addition to your own job as a platoon leader, is by observing, learning and being developed and mentored by the CPTs and other senior officers you will work for. Also, who do you think will actually have more access to the 1SG to get his advice and guidance as to what makes a good officer--an LT in the company or a SGT? As an LT you will be involved in everything at the officer level, whether it's planning, training development, disciplinary matters, etc. and you will also be guided and developed by senior NCOs.

So you will learn a great deal more that will contribute to your goal of having longevity as an officer by being an LT rather than a SGT. Because to have longevity as an officer you have to make CPT, MAJ and LTC. And the truth is you need to learn how to do that from successful CPT, MAJ and LTCs. You won't learn it from SGTs and SSGs. It's not a matter of intelligence or competency, but rather it's a matter of experience at certain levels of responsibility and perspective. A year as an LT will benefit you much more than an additional year as an NCO.

I'm a Mustang who had E-5 and O-1 promotion paperwork in my hands with the choice to sign one of them. I wanted the O Side as I completed my engineering degree. I've known a number of Stangs as well. It's a 2-edged sword. For as much as you learn drinking from the NCO fire hose, you'll have to unlearn about half of it. Lot of it has to do with different duties and different ways to get things done and more importantly getting others to get it done to meet the mission. If I read between the lines, you're trying to figure out the sweet spot in shifting over. My experience tells me you're pushing diminishing returns at E-5 and above. You likely are max on the O-1E opportunity at E-4. The real thing is the designator you're chasing, what the short program is for getting into it and then doing the long program of climbing the O ranks. Also consider staying around to E-6/7 can limit you to only LDO commissions when the time in service hits certain marks and you're capped at O-4/5. This is all Navy stuff but I presume there are potential similar hitches in the giddyup in the Army.

Bottom line, do you choose the Blue Pill or the Red Pill?