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.