The fees and conditions also can differ a lot, so you should try figure out first what kind of apple do you want (DP, LTV, rate) and then bring them to an apple-to-apple comparison to see which one gives you what you need for what cost (instead of accepting all the fruits that are on display from each different DSCR provider).  

Does that include covering your (future) retirement needs, health care costs, all other corporate benefits?

For holding vs. flipping, let your goals and market conditions guide you—flipping can build quick capital, but holding offers long-term gains.

We can apply for conditional use permits, or we can declare the new unit through zoning as long as it meets all requirements. 

He just wants to sell the house and use to $ to help his father with health issues, so he's willing to sell for under market value.

If your PM is only on Zillow than you selected the wrong PM, they are classified as a BOOB...Shelter is a necessity of life and there for it will rent but it will often come down to price and/or condition.

Risk is minimized due to the amount of rents, property condition, property price, and location.

This includes, water, hot water, heat, air conditioning, cable, security system, snow removal, lawn care.

How would you approach this given the market condition?

Because a 1031 is only available for a property you are using for investment.Here's the conditions.1.