Or possibly hard money or private money for a down payment and then repay over time. 

We also have a fairly unique relationship prior to working in the home together.

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1st... talk to a local attorney in your area and see if there are any regulations that are unique to your state, county, and/or city (or even subdivision in some places). 2nd... if the numbers work and you are up for managing six different tenants for a single property then go for it.

More specifically, how you stay on a positive repayment path without losing money.2) I would like to know how I can judge a potential renovation to be a good investment for a rental property or not.

There is no one stop shop to evaluate raw land as each piece of property is unique.  

Is there anything that makes your state/county tax unique?

@Martina Su If your main house is rather unique, it's always better to get a custom ADU to go along with it.

However, you are in a unique scenario where you already own the house and I am assuming you are paying for the renovation in cash and have not take on any additional debt.

If they are an expert in the property location and unique or challenging circumstances make it necessary to be creative in complying, then a code consultant can make the difference between municipality approval and not.