Is it even legal to make 5 simultaneous offers? I thought an offer requires a legal intent to execute, so that would make simultaneous offers illegal.

You could also try making an offer “firm and final, response due in 24 hours”, along with a cover letter stating, “I have 2 other houses I’m considering”. This lets the seller know while you love their house, you’ve got other options, and you will move on those if they try to counter.

Most of all, why are we even talking about offers in 2006? This conversation is for 2009. No matter what price you get today, no matter how lowball, it is still going to be 50% higher than what you would get in 2009, IMO.