Rural town but within walking distance to an elementary school, a high school and a nice restaurant.

  - Core Inflationary pressures remain high.

I generally rule out most single family homes as viable rentals, as prices are pretty high relative to rents, so aside from some downtown neighborhoods, typically you do not find large areas of single family rental neighborhoods (a median sale price on a 3 bed, 2 bath home so far this year in Dane County on MLS sales data is at $430k). 

With broad, high-level criteria, you may be able to easily cross of a number of neighborhoods where the numbers simply do not make sense (assuming you already have your buy box nailed down).

Knowing the three cities mentioned is important for grading the neighborhoods and can vary street by street. 

What caught my eye was how timeless your question is - high prices and tight cash flow are still big challenges here.

Unlike a kitchen or bathroom renovation your literally building a second house on the property and your dealing with everything from grading, soils, foundation, electrical, plumbing, framing etc.

Do you think that demand will be high for something like that? 

However, the high down payment and reliance on a DSCR loan could limit flexibility, especially with your DTI constraints.

I don't see how they could, since things happen... but again, granted there is no guarantee, these companies are claiming such high averages and they have such huge portfolios and good reputations, so it makes me wonder.