@Sergey Tkachev, I've been hesitating replying cause I'm dealing with a major case of survivor's guilt.  

Appears in pretty good shape from an online search.  

I'd like to retire or maybe semi-retire in about 10 - 15 years.I've been going through the BiggerPockets webinars, and hitting every online resource I could find for the last 2 months.I've settled on trying to purchase a Multi-Family 5+ building on Chicago's SouthSide.

You ccan search online what the average price is for a repair - IE- thermocouple for water heater. etcI think Cozy is a good website for basic PM stuff.  

What are the major variables we should consider? 

Second floor need some Renovations but not major.

I am sure you can research online the pros and cons of putting a commercial property under an LLC but the benefits are primarily both accounting and legal.

A tax lien state you are bidding on properties knowing that the large majority of properties will get redeemed and you will get a small percentage of properties.Most wholesalers buy lists of addresses and send out a mass mailing trying to connect directly with a motivated seller before their property goes to a public auction or gets on MLS.

Online EFT would be great, but I'm sure there's some old people that wont do that.

But I have done my due diligence in checking online their authenticity, as of now it seems to check out.