I hope to learn from the collective expertise of the members on BP and build a local team in Milwaukee. 

I recently had a infill lot under contract to purchase so I can build a 2 family house.

However, these buildings have no mortgages or liens and the areas have become quite desirable to young professionals since acquired.

I live on 5 acres and am considering building a DADU to use as a short or medium term rental.

The next thing would be connecting with a lender and seeing if you can find any properties that pass the self sufficiency test if looking at 3-4 unit buildings.

If you can find some common ground, continue building on that to establish rapport.

Keeping your building expenses separate from your personal finances can make it a lot easier. 

I would think of this problem differently: I might encourage them to explore ADUs... this would give them an additional stream of income and would likely only require a relatively small chunk of money in their savings (relative to the total cost).If they could partner with someone that has experience building and/or flipping (to qualify for the construction loan), then cash them out with a 30-yr DSCR loan (and use that as the builder's profit), then they could rent the property and enjoy the cash-flow.

I know people who did this so they could empty the building for condo conversions.

I reached out to several lenders about financing this project for the cost and renovation, I was either met with they only go up to 6 units, or the building has to  be occupied,  or that I was too in experience and I needed to put a license builder on the note with me.