I am in the army and applying to West Point. I wouldn't say that enlisting would increase your chances to gain an appointment. Really, it's a gamble because say you don't get in. You would have to continue your initial contract instead of dropping out. I don't know if it's similar to the army but I needed to get my company commanders endorsement. That took some time for him to view my worth ethics and overall soldier performance. Also, it's more than basic training. Straight after you go to your job training and the length of time is dependent on the job. Plus will you be able to complete all that trying and still be able to submit the application? It can take awhile to even go to basic. I enlisted October and didn't leave for basic till the end of February. That's something to think. Plus, bring enlisted might change your perspective on the military. I don't know your story but this is my two cents.