I've been frantically trying to get this deal in front of as many potential buyers as possible, not only for higher odds of assignment, but because the deadline for the EMD is approaching which could render the contract null and void.

Always great to do research and not rush too quickly, but its almost always better when people "make the leap" sooner rather than later like you said, I'd recommend at least putting some pen to paper on a date/deadline to do your first deal versus someday

Maybe sign your own lease (from Wisconsin Legal Blank, store in Milwaukee or order online) but keep it MTM.Also, a little brokerage 101: when you ask for something in an offer, always make sure it is specific, with a deadline and includes consequences.

They did not make an offer to pay rent/damages/legal fees before the deadline of the eviction. 

Either first come first serve or a deadline for all highest and final bids to be received.

Maybe give them an additional 24-48 hrs to vacate. if not vacated by this new deadline, let them know that you will begin eviction proceeding and it will go on their record making it difficult to lease in the future.

At first, he never responded to the suit though it had been delivered, and I continued moving the process forward, filing for summary judgement.Late in the process, long after his deadlines to respond had passed, he hired a small time tenant attorney to intervene.

Definitely a lesson learned to not pay in advance no matter what stage we are in the process/relationship that has been built.Luckily, I already met with three different contractors and all of them are wanting to finish the project within our February deadline.

Give a deadline for notification of their intent to sign a new lease or their plan to move. 

They may wish to keep their personal name private from the other investors, etc.One potential downside to investing in an LLC (and that I've seen has cause people to change their minds and switch) is that the tax filing deadline is a month earlier for LLCs versus individuals.