In California we have Prop 13 that gives owners who have had their homes for many years a strong incentive to stay put. 

If there is strong evidence indicating the Tenant was aware of the leak but failed to report it, then I would charge them.

Water and sewer cost are on me and IMO, that's a very strong deal.

In general details are not my strong suit, and I don't have a good system for managing expenses and keeping the project on budget.

The area that we're in has experienced some strong appreciation over the years and so this home has positioned us to have the option to keep it as a long term investment that we can leverage for our daughter's college or our family's future investments Lessons learned?

You'll also likely have to write a strong letter of explanation to explain why your properties went into forbearance and why it's not likely you'll go back into forbearance. 

I have strong credit and would be able cover the costs in the case the rental situation doesn't come to fruition, however where I am hung up is #1 - comping out properties in these more rural areas where there is lower volume and inventory to compare on a $/sqft basis let alone if the information is available and #2 - the majority of the properties I am looking at are older (built 1960s-1980s) some have cosmetic renovations but likely still old bones..this brings me to the my final point is building your 'team' I how have others found reliable inspectors, handymen, emergency services contractors, even cleaners for rental properties?

Having an R1 with an ADU would not create the structure that would allow for a common living space with the privacy of smaller units/rooms.

Depends on how the house is structured and how you feel about privacy.

Strong work.