Deadlynoob, I would win a game, just to make sure you don't drop (you're tied for 7th/8th at 1-13). 85% sure still means 15% unsure. The season I spent in Div III I was intentionally tanking to get a good draft pick and thought there would be a playoff to stay up (in which I could just play my best line up and win etc etc etc.). Obviously, since I'm in your league, good old IV.9, that didn't work out. There are a couple managers in our league who are looking to promote next season - I would not think your promotion is guaranteed if they all stay active. The ease with which people promote out of a IVth Division is typically due to it being all bots.
Oh, and I doubt you'll get BOTH of those guys. I'd be thrilled if whoever you don't pick drops down to me!
As an aside, I quite like this new draft system, although I would encourage people not to post ages and heights of the players they have scouted - it kind of gives things away...