I personally would put down 20 percent and keep the rest of my cash, even if it meant I wasn't "making money" in the beginning.

It didn’t feel right to return the deposit after property damage.

If you have any lending related questions, always feel free to reach out to me as resource here in Florida :) 

If anyone is interested I have a contact person who can provide more information. 

However, the person you spoke with has a good point.

I have a high credit score, good income, and money in the bank, but I have been having a difficult time finding a DSCR lender I feel like I can trust.

what you do with the money is likely less of their concern as long as they feel their position is secure in getting their loan repaid.

This particular strategy was personally told to me by Jimmy while we were driving from Phoenix to Las Vegas in the early 1980s to attend a real estate exchangers conference and exchange session.   

As you said, you do need a RE license to wholesale in IL so that would be a good first step.If you're still looking to house hack or pursue buy & hold deals, feel free to PM me and I think I can point you in the right direction.

Feel free to reach out if you need assistance.