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.  

We are buying two full rehab homes for <$25k in total - our strategy is going to be to fund the rehab with a hard money loan, build equity once the rehab is complete and then refinance the homes to get out of the hard money loans. 

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.

However, I think you're totally right that I can assist by helping him find his property first. 

-or conventional investment loan at 25% down ( I have just under 100k but with 25% down & rehab work I won't have much money left for other deals unless I use VA financing to move into a primary home (another 4-plex) then I could have 1 official investment property and 1 primary aka another 4-plex for a total of 8units)For the tenant situation, I'm thinking I should put them on a month to month lease for the time being since they are already living here and they can help me pay for the hard money monthly payment which is $1,584.98 while I get the 2 vacant units stabilized. 

The closest I can get to that over here in America is finding investors to do a CP loan on land where I will provide a list of suggested areas for sale, as well as the condominiums total 3D model with construction costs and all dimensions/specs provided.

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

Is it just 1.65% of your total profits?