Hi Miles,
Thanks for reaching out! My business partner and I both went to UVA so we’re always happy to hear from a fellow wahoo! And before I dive in to your profile, I’d like to thank you for your service to this country.
Starting from the top, your leadership experience, both in the military and in undergrad, is fantastic! The challenge that I’ve seen some military candidates have in approaching their applications is translating all that great leadership experience into civilian terms that the adcom will understand and that are obviously transferrable into the business world. So I definitely recommend having a non-military friend or family member (or a consultant!) review your essays and resume to help you check for that.
You’ve correctly identified your GMAT and GPA as soft spots in your profile. I would definitely recommend re-taking the GMAT, especially since the 690 was from your first attempt. (If it was your 4th attempt, I probably would not advise it.) You likely still have some upside in your score after further studying and drilling on the quant problems. I suggest taking another 4 weeks or so to really focus on your weak points then try again. Your GPA is what it is – you can certainly help offset it with a high GMAT and also through demonstrating analytical strengths through your work. If you have a compelling personal story as to why your GPA wasn’t higher in college (i.e. you were working 20 hours a week and/or were highly involved in extra-curriculars), you’ll definitely want to write about it in the optional essay for each school.
You have listed quite a range of schools. I’d be curious to understand how you put together this list. In general, school selection is best decided upon once you have really defined what you want to do after business school (i.e. a clear short-term goal that connects to a broader long-term vision) and determined what your other priorities are (geography, class size, culture, etc.). Of course, your final GMAT score will also give you an indication of what schools are reach for you vs. target. (That doesn’t mean you shouldn’t apply to reach schools, you should just balance out your list with reach and target in order to hedge.)
I just touched on this in the previous paragraph, but having a clearly defined post-MBA career goal, both in the short-term and long-term is a critical aspect to the MBA application. While you may be considering several paths, for the sake of your applications, you will want to narrow in on the most appealing one and really be thoughtful about how you see it developing. Entrepreneurship is a valid post-MBA goal, but what kind of company exactly would you like to start? How does it build on your prior experience/skillset? If you’d like to gain experience in the corporate world before starting your own firm, what job would best enable you to get that experience? These are just a few questions that you will have to answer as you develop your applications. These answers probably won’t come to you overnight

so it’s worth doing your research, understanding what the various paths are, try a few on for size, reach out to friends and family for advice, etc.
The last comment I have is on timing. I think that it will be very challenging to make the R1 deadlines for many of the schools you listed. In order to do your application justice, really take the time to make sure it’s perfect and don’t pressure yourself into R1. R2 is no more competitive than R1 and you’re not impacting your chances at any of the schools by delaying to R2. I always advise my clients to submit their apps in the round when they’re 100% ready.
I hope this was helpful! I know I threw a lot at you here but the MBA application process can seem really foreign and daunting, particularly for applicants coming from non-corporate backgrounds so I wanted to give you as many pointers as I could.
Always happy to chat further if you’d like!
-Melody