Off Market Deal located Chicago, Illinois

[Raymond Punzalan]

Hello BP.  I'm a real estate newbie and interested in purchasing my first off market rental property East Irving Park in Chicago, IL

Its a multi unit property (2 units and basement).  First floor (2 beds/1bath) Second floor (2 beds/2 bath) Basement (full bath)

I have a couple of questions:

1.  The basement is not able to be legally rented out since one entry.  The current owner consistently rents it out on Airbnb.  He mentions that airbnb charges $5k licensing fee (for every unit) and owner needs to live in property.  Anyone familiar with this?  I can maybe find a referral or family member or student on craigslist (short term) - but I don't want to risk it and I don't to start my first property with this inconsistency?

2.  I mentioned to owner about seller financing and he is open to the idea - although would prefer to go through mortgage company/bank. How can I lean into this so that he is more inclined to consider this option?

I'm still learning to analyze this deal, but any other information would be helpful.

Thank you!