Never really sure what the future holds, but I would like to hold for cash flow. 

There is a difference between profit and loss and cash.2.Each investment is reviewed independently from profit and losss, as you make more you can have greater down payment but the profit from it is always based on what you paid/have into it.

If rent is greater than PITI, they believe they have a cash flow positive property.  

It isn't unrealistic at all to expect $15k cash flow from that and that provides a cushion in case of other issues with the long-term rentals.

My desire is to create profit by commercial units or owning multifamily units in order to provide housing as well as generational wealth.

I can definitely tell you there's still a lot of positive cash flowing and 1% rule deals and you get amazing appreciation.

Can someone provide your thoughts on the following questions, please? 

He has acquired the land, gotten the permitting, has construction financing lined up but needs ~20% cash equity / home.I know very little about his particular real estate market, and I've never built anything myself. 

They give me an Owner Statement each month with all the details like Beginning Balance, Cash In, Cash Out, Owner Disbursements, Ending Cash Balance, Property Reserve, and Net Owner Funds.It’s super helpful, but it doesn't cover all expenses, and I need to get all this info into QuickBooks.

The property currently cash flows a little over $500/mo.