Should I enlist and then request to go into OCS or just wait and try to get into OCS before joining the Army?

(Join to see) the age limits, even with federal service waivers, move with accessions needs. Being a LT is a young person's game. It is also demanding and learning the Company grade craft is taxing. If being an officer is your goal, I'd take the most direct route. If it weren't feasible or acceptable, there wouldn't be a Civilian to OCS program. I'd just say get on with it. If you have doubts, then don't.

If you enlist first, life will happen: marriage, injuries, children, mortgages, bills, deployments, overseas services, etc. right now, you are unencumbered. My two cents.

I think you should go for a spot at OCS first. You have no guarantee of ever getting an OCS slot if you first enlist. But you will know you will have a guaranteed slot if you try first for OCS (although you still have to go through Basic in the Army). If you go Reserve or Guard, then you have a guaranteed job as well as "priority" to getting into Federal OCS at Benning once you complete Basic.

Here's the deal brother...If you want to be an Officer "off the street" it is defiantly "doable". Without delving in to the "prior enlisted" versus "off-the-street" officers, both are attainable. Enlisted guys look more favorably on officers that served as enlisted first but that's neither here nor there.
Work with what ever recruiter you're currently talking to but expect that you'll bear the brunt of the leg work involved (full or 2/3 length photo, letters of recommendation, going to MEPS to take you ASVAB and physical, etc.). Most recruiters are hard pressed to put people in the Army and to be clear officers take a LOT of time - ergo you should do the hard work lest they steer you toward enlisted jobs (AGAIN - not bad per se, but perhaps not what you want). While this isn't a bad thing, it may belabor your being an officer. Becoming an Officer off the street can take anywhere from 6 months to a year factoring in the packet, physical, training, etc....and that's the conservative side of planning - Being enlisted means Basic Training, job Training, first assignment, etc....AND assuming you're still motivated putting in your packet after a year of performing your enlisted job and going through the motions needed.

In both cases, being an officer is attainable and BOTH depend upon your tenacity and work ethic...Many people aspire to be officers through BOTH avenues but frankly lack the stones to get it done. Ask yourself first and foremost HOW important it is to you, set your sight aperture accordingly and DO IT.

Great question. I don't think there is an easy answer. Here was my thought process as someone who joined the Army at age 23 with a bachelor's degree. At the time, I had no desire to be anything more than a "one or done." Considering my options, the enlisted side actually had much better life skill training opportunities (I learned Arabic, went to college accredited courses for analytics, etc.). It also came with a bonus that earned me more of a salary in my first 4 years than a 2LT would. So I enlisted first. When I re-enlisted the second time as a Staff Sergeant, it became apparent to me that the Army was probably my career and I needed to make a big decision as to whether I would be a career enlisted, Warrant Officer, or Commissioned Officer. I chose the officer route, went to OCS, and here I am. Advantages: There are things BOLC does not have time to teach that are really essential such as NCO/Officer relations, property, legal stuff (because as an officer, someone will make you an investigating officer of something many times), mentorship, counseling, deployment operations, and some others. Being enlisted first gave me a huge leg up as a platoon leader / company XO when dealing with these things. Disadvantages: If I am fortunate enough to make it past Major, I will be a LTC in my 50s where most people on track will make it in their late 30s to early 40s. It was also hard for me to lose the NCO culture from my brain but that's not necessarily a terrible thing. At your status in life, I think I would just go ahead and put in for OCS. Already in your late twenties, if you enlisted first, the value of doing so would not be complete in my mind until you are at least a Sergeant, so about 6 years after enlistment. So if you enlisted first, you wouldn't think of OCS until 33 or so. If you current plan is to enlist first and do anything less than 6 in the enlisted corps, I would say you should skip the enlistment step altogether because you are not going to get enough exposure in the enlisted ranks to truly augment your officer career.

If you want to be an officer, and qualify, do not enlist.

Can't speak for the Army but I served in the Marines with another Sergeant who had his degree and a recruiter convinced him it was the "quicker" way ti become an officer. He was told that the OCS class wasn't starting for close to a year and that if he enlisted and completed basic that it would give him a leg up on the competition. Four year enlistment and he never got any help and reached his EAS as a Sergeant

Choose OCS first. You are a commodity to your recruiter as a potential recruit. They will jump through hoops to get you in but once you are, it is a lot harder to get things done.