This is very old but curious if you were successful with this? 

Sounds like you’ve put in the work to build a solid foundation—wishing you success as you take the next steps!

@Alex Fenske - Amazing story, congrats on your success.

Structuring the deal properly (like through a land trust) can reduce this risk.Your best bet is to connect with an Illinois investor who has successfully done sub-to deals or find a local real estate attorney who specializes in creative finance.

Quote from @Jeff Roth: Hi Lina from Texas-Congratulations on your interest in investing in mid-term rentals and you are wondering how and where to get started.I get this question frequently from investors.Sometimes and investor is looking to keep their property cashflow positive as insurance and taxes have squeezed cashflow by turning units into mid-term or short-term rentals.First off, ideally, the property will cashflow as a long-term rental should something disrupt the mid-term rental model.You will also want to have the property be near where there would be a demand for mid-term rentals (hospitals, universities, research centers).Monthly rents for mid-term rentals are about 20% (+/-) higher than unfurnished similar long-term rentals.There are property managers that will manage mid-term rentals for you and I always advise my clients to use property managers to keep their investment as passive as possible and for compliance issues related to Fair Housing Laws and local regulations.To Your Success! 

 Do you believe you can achieve a better result for your family member trying to sign an assignment contract over retaining the best real estate broker in the market with a robust marketing package while leveraging the sales professional's relationships?

On the flip side, learning how to deal with those problems sets you up for a successful life regardless if you stick with realtor work or not. 

Look into a DSCR, Debt Service Coverage Ratio, loan where the rental income can be used to qualify the cash out refinance instead of your personal income.To Your Success! 

It's great to hear about your success with this multi-family buy-and-hold investment.

Networking with local investors, agents, and property managers will be key to your success.