I maintain even break even on valuation (which is rare in SF Zoned areas), the ADU has big disadvantages versus new property acquisition including financing, level of effort, rent control, prop tax being based on cost rather than value added, length of time including length of time from first expenditures to first income, reduction of something from existing unit (in your case existing home lost its garage).Did you see starting next year Mf can add an ADU per unit up to 8 units without any affordable housing concessions?

If it was me...I'd check with zoning to find out how many dwelling units I could build, and I'd find what the requirements are for those units (type of house, height and setback restrictions, etc.).Then I'd find out what local builders think the cost to construct would be - just get a cost estimate per square foot for 2 or 3 different levels of finish.

Quote from @Levi Perl: The purpose of background screening is to determine a level of risk, and then you decide if you can mitigate that risk.How does a DUI conviction from three years ago impact the tenant's ability to pay rent or maintain the property?

If the score does not seem to be backed up by enough credit history to be reliable, I will make a judgement about the tenant's level of responsibility based on their answers.

You've earned $132,000 more by splitting your money and leveraging it.Since I've been searching for more deals I have seen one or two that might actually cash flow decently but most seem to be at break even assuming normal expenses, vacancies, etc.I'm just learning my comfort levels with leveraging and trying to take advice from others about managing multiple low cash flow properties vs. one higher value one. 

I think behind tenant screenings and leases there is a quality of a landlord that's also as a person that is the respect for a good person and the intelligence of making fair affairs.For me for ten years in the past I had a house of 650sqft (two rooms and cozy kitchen) where I always have been giving away one of the room for others who were asking for help for themselves and I didn't had any earnings for me by that, and that has been during for many and many years, meanwhile I was surely needing more space for me, for my business in a studio and for my own personal life I eventually could have been having.Nonetheless this, on last years I had no more an house and I needed a room for rent, but even before any screening the landlords were being unrespectful and very unreasonably severe to me, they often had making me lose so much time by no taking or going away to the point I had no other choices in the end, and they set me in the wrong places for me, dangerous ones, too small, too big and very expensive, unhealthy ones or not providing anything at all when it was obvious they needed to.To me this kind of behaviour is very wrong, mostly because usually they are the same people who pretend respects and acts as they are very careful and attentive to housing situations in general, but with me, they have been lying above anything and just disrespected the person at a human level. 

What is the appropriate level of cleanliness to maintain during project work?

It seems counter intuitive to call for that level of development, and then turn around and throw landlords under the bus during the Covid crisis.

If they are changing jobs, they need the new job first and you need to paychecks or offer letter with salary or maybe even the first two paychecks at the new job, depending on their level and income.Ask them about deposit and rent. 

That helps bring back down you debt to income level.