Chicagoland is extremely tenant friendly so understand that going in. 

Rates may still be high, but sometimes they’re more flexible with repayment options than a mortgage refi.Family Loan Structure: Since you have an existing interest-free loan from family, you could talk to them about restructuring or even adding onto it, if they’re open to it.

That said, if managing sounds overwhelming or you’re strapped for time, hiring a property manager from the start is a perfectly valid option.

I would budget maybe 20-30k depending on how far you are going down.

If you are hoping that this property will stand on its own with you living in it and not having to put your active income into it, then it might not be the best option for you right now. 

We have several vendor business members in the title space that are very investor friendly.

They have lots of options for you, depending on your budget.

Budget-Conscious, ROI-Focused – A great designer knows where to splurge and where to save.

Once they are leased, then you can take over from there.There are several software options if you want to self manage.

My wife and I have a vacant lot in Tallahassee and we're looking to use the current equity to exchange for a larger single family investment property. The lot is paid off and deeded to our LLC, but lender will not do ...