I understand the concepts and procedures of wholesaling on a higher level pretty well (assignment, double close, etc), but I'm not sure of the EXACT steps to take in the process.  

The main challenge is to give clear operating procedures to them so they can accomplish what you need them to do. 

Hello BP community!I've been experiencing my first eviction and hopefully last. Now that the tenants are out, they owe me a good sum of money (no rent paid, damages, etc) that the security deposit wont cover. Although...

The easy way: O conveys to E via deed in lieu.The not-so-easy way: judicial or non-judicial foreclosure, depending on what the underlying docs were.The hard way: declatory judgement in district court.The really hard way: declatory judgement in probate courts, with a side of procedure to determine heirship.There may be other options, depending on what other facts are relevant, but this is a sampler of what it takes to clean up issues. 

Sounds like that village needs to revise their transfer stamp procedure.  

You can make them aware that neither of them is in risk of being ousted, you just want to make sure that you've followed your business procedures. 

If not, I would talk to your landlord and just vaguely ask about what the procedure would be if you needed to break the lease.The part that might hurt you is your lender looking at that fixed expense, but that will be specific to the lender. 

I wouldn't mind starting out on the debt side at all, to learn lending procedures and secondary markets.

Take a look at the lease agreement and go over the move out procedure expectations in terms of cleaning and damages. 

If you do move forward with an eviction, you'll have to abide by the letter of applicable laws, which include the Illinois Code of Civil Procedure as well as municipal laws within the City of Chicago (or whatever municipality you may be in).