However now that it's been a couple years and Avantstay is running these like a well-oiled machine, I probably will continue with them as a PM company when my master lease is up. 

I just got signed up with Rent Redi and would like to import the previous  monthly rental payments into rent redi to have it correctly dispalying the lease terms with rent owed.

I would like to start close to home as I plan to self manage the rental side of it.

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.

Nothing to go crazy about but it feels like a "win" for three generations of my family in this difficult market. 

I’m likely to receive a promotion at work in the next year which comes with a higher salary.

Or like many small in businesses you raise cash from friends family and anyone else that knows loves and trusts you.The other thing I suggest is to make that $27,000 or $37000, or $50000 yourself over the next year. 

I’ve been involved in property management for over a decade and have a passion for optimizing operations, maximizing cash flow, and creating great experiences for both tenants and owners.I joined BiggerPockets to connect with like-minded investors, property managers, and real estate professionals.

You may do some research on what life is like on both ends and make a decision from there. 

Approach it like an investment.