Jigsaw - If you're really good at puzzles and riddles, this might be a tempting option. However, jigsaw rigs his game in very sinister ways. Sometimes you have cut off limbs and other crazy shyt. You might bleed out or be limbless by the time you're done.
Freddy - Can you stay awake 7 days. "The easy experimental answer to this question is 264 hours (about 11 days). In 1965, Randy Gardner, a 17-year-old high school student, set this apparent world-record for a science fair. Several other normal research subjects have remained awake for eight to 10 days in carefully monitored experiments."
The problem is, you can easily, easily fukk around and doze off.
How Long Can Humans Stay Awake?.
Apparently getting drunk will stop you from entering rem sleep, so that's another way to stop Freddy.
Most of these guys can kill you while you're asleep, but Freddy will at least let you hang out and try to stay awake.
Jason Vorhees or Michael Myers would be the hardest to survive, outside of Jigsaw. It would be near impossible to stop them. You would constantly be on the run day and night and would probably succumb to exhaustion. I would try to trap them or trick them into going into the water, and hopefully they get swept up in the sea.
Dracula you have a good shot at if you can kill him while the sun is out on the first day. If he survives the first day and awakens at night, it is going to be very hard to survive the night. It would possibly be worse than any other option, because you won't be able to outrun him.
Don't know much about Damien or IT.
I'm going with Freddy and setting up some sort of anti-sleep mechanism. It would be extremely uncomfortable, but it's probably the best chance to save the fam.