When should you get your degree (military)?

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The answer depends on the individual.

Getting a bachelors prior to enlisting will get you E-4 in the Army.  It won't get you anything more than an associates would in the other services.

It is the minimum requirement to apply to be an officer, but a whole lot more goes into that selection process.  A 2.5 GPA in art history isn't going to cut it, but a 4.0 in a STEM major, with a lot of other good stuff on the application will.  Of course, if you don't want to be an officer, it doesn't really matter then.

If your end goal is to enlist, then just do that.  Use tuition assistance while you are in and the GI Bill after you get out to get a bachelor's for free, or close to it.  

If you aren't really sure if you want to enlist now, then maybe finishing your degree is a better option.

With a bachelors you can apply to be an officer.  With an associates, no.

You have multiple options if you join the military. You could use the benefits to pay off your current student loans or you could use the benefits to go back to school for free. 

I chose to get my degree after I served in the military and not only was it free but I was actually paid to go to school. When you use your GI bill you are given BAH allowance (Basic Allowance for Housing). The amount you receive is determined by the zip code where you live and/or attend school. I took exclusively online classes full time which only allows half of the normal rate to be given. If you take in person classes full time you are given your full BAH allowance. Base on my zip code which is a rural one, a full BAH allowance would have been $1600/month, but me taking only online classes reduced this to $800/month. If you live or attend school where the average cost of living is higher your BAH rate will increase.