I was active duty for 4 years, now I have been guard for a little over 2.

The VA might be diagnosing me with OCD and ADD (I definitely have both), but I am afraid of pursuing it any further because I dont want it to compromise my military career (especially because I am a cunt hair away from making E-6).

Will being seen for OCD, ADD, or getting Medication for it effect my my career? Ability to deploy again, etc? I know these can be issues if you are trying to enlist, but I am currently in.

Not sure about the army, but in the CG as long as the ADD can be managed with out Ritalin or aderol you are good to go. Not sure about the OCD though.

I know tons of dudes on adarall (sp?) that get it from the base behavioral health

Add meds are fine.

OCD I'd have to look at the regs more.

AR 40-501 has no problems with it. I forget where I read that Ritalin use in the last year disqualifies you for deployment, so that may be a starting point.