You may want to find out what you can legally add to a future lease.

But most of these bridge loans have future funding components where the lender will fund renovation work as the work is completed and add that to the loan balance. 

Legislators often leverage future obligations in the form of bonds.

This might be a question for our insurance broker/future attorney, but wouldn't the LLC be formed in Indiana since the rental property is located there (versus Illinois where we will be living)?

There are several ways to find out which cities/areas cash flow and get a good idea of things like market rents, ARV potential, and future appreciation.

I have a wife and 3 kids and the weight of their futures on my back.

Large Metros get this.You should be looking in growth markets which have higher cap rates - but the future projection is they will decrease.Mid-west for instance. 

House hacking is going to be a great starting point to building your wealth that you can leverage in the future. 

Focus on undervalued properties, prioritize high-ROI renovations, and refinance to pull equity for future deals while maintaining 20-25% equity.

We are hoping for a future that would include developing a co-op.