Just out of curiosity, is this hypothetical doomsday scenario based on any real timeline in the past? On some levels, it makes me think of 2000-2002.
In my case, from 12/31/1999 to 12/31/2002, I think I did lose about 45%. However, the true severity was masked somewhat, because I didn't have a lot saved up by then, and at the rate I was investing, the additional assets made a difference. I actually hit an all-time high in May of 2001, and then by September 2002, I think, it bottomed out. So while technically, I had three down years, the actual "crash and burn" period was only about a year and a half.
But then, the following four years were nothing but up. 2003-2006 were excellent years for me, aside from a ~10% pullback in the summer of '06. And again, this was also helped by the fact that I was (and am) still working, and contributing, rather than having to withdraw.
FWIW, I think a cycle that would repeat retiring on 12/31/99 would end up being a failure cycle for me, or at least, one that would require tweaking. Using a $1M starting balance, and using actual inflation numbers, plus my personal rate of return over those years, a 4% withdrawal rate would have me down to $287K as of 12/31/17...and withdrawing about $58K per year. So that scenario, obviously, couldn't go on too much longer. This also doesn't take SS into account though, so if SS comes online for you soon enough, and how big that check is, this scenario might actually be workable.
A 3% withdrawal rate would leave my portfolio at around $817K on 12/31/17, and a withdrawal rate of around $43K per year, thanks to inflation. I think that one would be pretty safe, especially if you factor in SS.
4.5% would have the portfolio down to ~$27K by the end of 2017, so obviously that one's at death's door, and just about to ring the bell. a 5% rate would've had me out on the street a few months into 2015.
I also ran a set of numbers assuming I retired on 12/31/07, just before the "Great Recession" hit. That 2000-2002 period is actually more damaging, to me at least, than the Great Recession, because it dragged out longer. As a result, the balance never got a chance to recover enough, so the Great Recession knocked it down again, to the point recovering again was just about impossible, except for the most conservative withdrawal rates.
Of course, your mileage may vary. I was (and probably still am) invested a bit risky, although I'm almost to the point that dividends could cover my basic living expenses, if necessary. And, if they don't get cut!