It usually takes multiple interactions to build rapport before meeting in person 

But, commercial tenants, as was said above by @Greg Scott, can create longer vacancy times and may want build outs done, depending on the area and the prospective tenant.At your price point, the spread on commercial/residential will matter also based on your management expectation.

I currently have a place I rehabbed that I have listed for sale because I'm also building a house that I need the cash for, but I have another house I just started that I may rent.

It would take me 6 months to fix our primary up and an additional 6 months to build the garage.

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.

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

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.

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.