I never bothered to change my DD-214, mostly because I've exhausted all the VA benefits I'll likely ever use. But, I don't believe the feds have any significant issues with name changes, etc. There was nary a blink when I changed my name and sex on my government-issued pilot certificate. There were no issues obtaining a passport.
I'd go for it, but I'm not in your situation. I think the worst they could do is request more documentation. If you decide to change your DD-214, I think doing so before the November election is probably advisable. If Cruz is elected we'll end up with all three branches of government under the control of extremist social conservatives. Who knows what they'll do with their new-found power?