I have no family-oriented background in real estate but I have a personal aim to inject this into my family's heritage starting with me as the first generation investor.

Some ideas that come to mind: -Yeti style mug or Swell water bottle with your logo on it (filled with candy). 

I was thinking (and this is where I need advice) on purchasing the property and renting it out “Airbnb” style since the building allows short term rentals. 

I don’t know your market or your negotiating style, but imagine if you do get the property for less money and it cash flows better?

I personally wouldn't over complicate your lending with commercial style loans (and guessing you wouldn't qualify unless you were doing some type of multi-family or portfolio project). 

examples: Type/Size of house - (so we know what you flip using this kit)Paint color/brand indoor-Paint color/brand outdoor-Flooring type/brand -Cabinets type/brand -Counter top types -Pulls (style, type, etc.)

That's not my style both because I don't want to be a slum lord and because I'm not investing in Detroit purely for cash flow.Yes, I know Ashley bought dumps in that price range and fixed them up and now they're worth more.

The 70K is for the lot and the cabin (Ikea style).

At least more so than a set and forget style syndication.

I'm in Jefferson Park, which is definitely a family-oriented neighborhood of Chicago.My question is: If you were me, would you rather own and rent a 3 Bed/ 1 Bath or a 2 Bed/ 2 Bath?