Is there something specific about this cabin where the furniture is going to determine the success of the STR? 

There are so many things that can go into determining how to interpret a contract.

Determine that you'll conclude your analysis by (some date), giving yourself time to get any estimates you need from contractors or suppliers for the rehab.

You also would need to properly account for all of this.You would want to discuss your specific situation with a qualified CPA to determine if this can be done and if it really benefits you any.

We were told they have researched the Chicago area and safely determined there's at least $20,000,000 of real estate that meets their criteria. 

You have to take information you independently verify and determine what your risk is from that information.

I do the analysis and determine what a payment would be and what cash flow would look like.  

One of the most important aspects of wholesaling is determining that the seller has the authority to sell the property.

I have basically 1) rewarded poor tenant behavior 2) tenant has no eviction on their record making it more challenging for a LL to determine that the tenant has been paid before and seeing it worked so well is likely to repeat the same $hit.  

Hey Jake,You'll definitely have some options with DSCR lenders, but you'll need to be really sure that the lender you use is okay with underwriting STR income as well as with the ADU as a mid-term as they are kind of tricky.With DSCR loans, your credit score is going to be a big determinate to where you will lend.