Should I Retake Prereqs?

Unless you retake those classes that you received Cs in, you can't say that you have a 3.81 uGPA. Your uGPA is whatever is on your transcript with those classes and if you retake and get all As, under the osteopathic system it will be what it will be with those As substituted. In short, you have to include those Cs until you replace them.

You need to take the Medical College Admissions Test. What is your knowledge base for this test? Since many of those classes that you plan to retake have knowledge that is tested on the MCAT, you may need to retake for the purposes of making sure that you are well-prepared for this test. No osteopathic school is going to take you with a poor score so that doing well on this important test may be of paramount importance in your desire to get into osteopathic school.

Calculate with and without retakes in those courses so that you actually know where you are and where you can go. Many people get into medical school with Cs on their transcripts but you may need to be sure that you have a solid grounding and knowledge base for the MCAT (easier said than done). There have been plenty of people who had As on their transcripts that "hit the wall" on the MCAT. Don't underestimate this test and be realistic in where you stand within how competitive you are for the schools that you want to apply to.

If you are not competitive, then get yourself competitive by whatever means necessary. If you have to work and support a family, then don't expect that this will be an easy process. Is it doable? Yes, it is, but go slow, do excellent work and keep your eye on your long-term goals.