Sorry I'm so late to this thread. Hopefully Matt hasn't changed his mind and decided to enlist now.
Matt, I was enlisted for a little over 3 years before going officer. I understand the appeal of possibly getting your college loans paid although that program is surely on the chopping block right now with the pending budget cuts. The chance of you even being able to apply to OCS as an enlisted man is slim based on the numbers who want to apply. Enlisted men have to request and compete just to reenlist, regardless of how shit-hot you are. If I had it to do over, I would have skipped my enlisted tour and gone straight to OCS.
Let me give you a simple example: I made over $135k last year as a senior LT/O-3 living in Hawaii with just under 10 years of commissioned service. $15k of that was a bonus so my peers who didn't take the bonus made $120k. With 10 years of enlisted service as an AW, I'd expect you to be an E-6, best case (AW is very competitive). An E-6 aircrewman with 10 years living in Hawaii would make around $83k assuming you're married by then. Bonuses aside, you're looking at nearly a $40k/year difference in your wallet without even considering the tremendous difference in quality of life between an E-6 and an O-3.
I would highly encourage you to apply for OCS. If not selected, apply again and again! Enlisted men do a fantastic job under less than ideal conditions. Do you want to work harder for significantly less reward given the option?
Lastly, which AW rate did they guarantee you? AWR, AWO, AWF???
Best of luck!