You are kind of assuming that everyone is as settled and organized as you.
Obama was not an attorney in 1986. He was just a student. Since then he has traveled between Hawaii, various addresses in New York, Boston, various addresses in Chicago, etc. He obviously didn't carry a safe or a desk around with him during all these moves.
Speaking for myself, like Obama I grew up far away from where I now live and have moved many times. I found my BC in the home where I grew up and just left it there because that was a safe place until my parents died. I'd like to have it but it's probably in storage, so it would take a lot of effort to locate it and it is very easy to order a new one.
With Obama there are several possibilities:
1. When he found the BC he kept it and took it with him to all those addresses and amazingly he still has it.
2. When he found the BC he kept it and took it with him to all those addresses now he is not sure what became of it.
3. He found the BC while visiting his mother or grandmother and left it for safekeeping with them. After the death of his mother it ended up with his grandmother or maybe it is among his mother's papers that are perhaps held by his sister. Since his grandmother was a banker, maybe she put it in a safe deposit and it's still there until her estate is settled.
4. Etc., etc.
In any case he should still get a vault copy from the Hawaiian DOH. His avoidance of this is very odd.
I did follow up the post with a quick post to state that he was “an aspiring attorney/POTUS” - not there yet, but at any rate not some schlep without a clue - frankly I would expect that most who rise to such high positions are pretty detailed and organized. (would be an interesting study for geeks like me)
Also, don't get hung up on the “safe”, “desk” issue, the point being that people typically keep important documents in a specific spot/receptacle that they know of and can access. I know of very few (if any) who don't - it is typical human behavior - even you know where your original BC is (although not so easy to access).
As for being settled, you are assuming I am. In 12 years I lived in 6 different cities and 7 different residences in the Midwest and East Coast. Changed schools as well. (My cert also resided at my parents for a short time after I left home.) Organized? I try to be but at any rate I've always known where my 1-2 files of “important docs” were. I don't see it as “amazing” that one would still have their BC after moving around.
As for Obama and what he did with the “1986” BC: as I said, maybe he lost it. However, 1) it is an important document for anyone to have and keep tabs on; 2) for him, it was important enough to mention in his book (even though he could have just gotten a copy from the State - kind of an odd thing to say if you think about it, unless the one he found was different from one he may have had or seen - he did go abroad in 1981, and he also likely needed one for Bar admission later but before he wrote the book...); 3) it was even more significant for him than most because of his father and identity issues - again, enough that he mentioned it in his book. Therefore, I find it hard to believe that he would have misplaced it (although he certainly could have).
It could definitely be with grandma's estate or in box or storage in Hawaii- but there again, it raises the question of: why not just go and get it from there, rather than go to the State? Both in Hawaii. In fact, if it was sitting in a safety deposit box or box/file at grandmas and he is now a grown man with a family, and she is getting old, and people are asking for it, and given the personal significance to him, why not go get it and produce it and then he'd have it - it would seem just as easy as going to the State.
In the end, who knows but him? But it is a reasonable avenue of questioning. Time for bed. Goodnight.