Listen, it's certainly not a sure thing, but here' my thinking.
256 league champions in DV that are ahead of him. Fine.
64 DIV leagues, means 64 promotees. 4 teams in each league that demotes (8 place in each conference, plus the loser of each conference's relegation series), that's 256 right there. Combined for 320 open spots.
16 leagues in DIII, times four demotees in each league is lucky number 64 teams coming back to DIV. That leaves exactly ZERO spots left. Perfect wash.
BUT. In my experience in DIV, there are tons of bot teams. Heck, we had two in my DIII league. At least 25 teams are bots in DIV that do not fall into the relegatin series. This means DIV will need at least 25 team up from DV.
I think with his record, he's in the top 25.