The questions pertain to how to structure ownership, how to divide income/expenses among family members, how to minimize individual tax burdens, etc.

Yes, all deals are in the Bay Area.Learn to play the game well while learn to minimize your risk.

This is where my questions begin:I am looking at finding a property or two that can be used for MINIMAL cash flow in the first year - obviously both come with a little risk but wanting to put as little down as possible - to have some in reserves if it takes a while to build up or get rent coming in: for your knowledge these units are in the greater Chicago land area.Option 1 - 1 bed 1 bath condo - Investment Property - Listed at 170,000 good shape - needs no work and could be ready for rent right away - currently empty - looking at about $34 down plus closing costs (another 5 or 6K?)

This house is around 700 sq/ft with a sagging roof, 1 interior wall separating this area with the kitchen, minimal floor joists, hardly any electrical and no plumbing.

You might have been living in the blue pill state for years maybe decades so take it slow.Understand the men are from Venus and women are from Mars.

Key is to minimize them.

I'm looking for a way to help him keep a beautiful home with minimal risk to either of us, but hopefully also make a small return in the process.TLDR version: $1M property value, approx 15-20% equity.

I would say bigger is better when it comes to DCR so to minimize downside buy a more stablized, cash-flowing asset with strong in-place CF.

Expenses are minimal (Maybe $3-5k for the year is our estimate).

So we have a tenant that we inherited who is paying minimal below market rent for almost 3000 sq.ft.