Do not offer to pay more rent ever to make the deal happen.   

But it might make sense to work with folks who can offer more focused guidance on filling the knowledge gap you have.If you shoot me a DM, I can also ask around for more of 1:1 coaching opportunities. 

My goal is to live in the home during the winters, maybe 3-4 additional weeks for vacation, then rent it out to help cover the mortgage the rest of the year.  

I second @Erik Estrada Chase offers great programs for business, multifamily, and conventional loans for commercial properties.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

You will likely need to rehab for any strategy but Co-Living will be more bedroom additions which is less cost compared to kitchen and bath remodels that are more needed for furnished rentals. 

I see what you mean about offering a higher return to a potential investor, especially if they are not familiar with my character/experience in the industry. 

We might have an offer as an AITD but also want to know if we should even consider an offer like this.

However, the concept of a virtual office is a very useful tool that provides a professional fiscal and commercial address, as well as additional services such as mail handling, meeting rooms, and phone assistance.

I know I could have a family member co-sign a mortgage with me but not sure the best way to approach that conversation and what incentives I’d be able to offer to make it worth while for them other then their “familial duties” haha.