How much preparation is enough to successfully transition out of the military?

Depends on the person I think.

In my case, I had spent 36 years PRIOR to military service as a civilian. I had experience buying big ticket items like cars and houses, had savings and investments, had civilian jobs/career, raising a family, and already had graduated from college; so I was already very well positioned to move back into the civilian world from Active Duty.

Contrast that with those individuals who may have spent 20-30 years Active Duty military, having joined at age 17 or 18 knowing little of the (adult) civilian world, and the transition back to being a civilian would not generally be as smooth. For them, they should be afforded as much time and resources as they need to make the transition.

For the vast majority in between the above two extremes, it comes down to the individual and their level of experience in the world outside of the military. But transitioning I think helps everyone to some degree so long as they are willing to buy into the program. While some of ACAP was rudimentary and repetitive info for me, some was quite helpful in transitioning and landing a civilian job. So long as the resources are there, everyone should be afforded some level of transition help--and reasonable time to process--regardless of how easy one may think transition will be for them. For some, that help can be a life-saver.

Honestly, this should start from day 1 of joining. Had there been better tools available, I would have made different choices in the types of assignments I took and the prep I did for ETS. I think the biggest problem is that there are not enough resources available and what is available isn't exactly good. I never even got an interview using the resume I did in ACAP.

I'd say a couple months at least. First and foremost, you need to be able to lock down a job. Once you have a job, then you can pick an area to look for housing. Once you have housing setup, you'll be able to schedule your government move. Hopefully that's all you have to plan for.

When I got out, my daughter was scheduled to be born 2 weeks before my EAS. I had a full 2 months of leave saved up and even 2 months before that I was applying to every job I could in a 2 state radius. Once I snagged an opportunity, I had a geographic location to look for a house. I was searching in a 3 town radius because I had to not only find a spacious house for my growing family, I had to find a place that was pet friendly for my dog. I came across plenty of bad neighborhoods, or places that discriminate against dog breeds before I found a decent place. Then it was just a matter of setting up my move which is always a hassle.

Thankfully things went well, but mainly because I wasn't stressed under time constraints. If I had even less time, I might have been stressing out a whole lot more.