I understand that if I rent this ADU out, then I can have a tax write off on the mortgage payment and insurance payment for the the ADU's sqft portion.

The ideal home price for you will depend on: 1) downpayment size 2) risk appetite, 3) preference for more cash flow or appreciation.Given our price points, our investors need to have 35-45K to start, on average.The typical cash-on-cash return on our properties net of loan payments, insurance, taxes, and property management fees is 6-8%.Ultimately, you can obtain financing from any lender, although we have partner lenders that can provide very competitive rates.

you probably know this but - there are holding costs associated with most flips - interest on the loan, insurance, and sometimes others depending on the localityhope this helps 

And typically long term rentals don't make it easy to include property management fees into the numbers and have them still work well.I would consider looking into STR type areas where you can avoid the risk of property damages (str and pm insurance covers almost everything that they might damage) and evictions/collections.   

My insurer is Erie, for everything including my umbrella. 

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

Or if your not doing too much volume he can buy/partner in his personal name and get good liability insurance.

I’m a Colorado commercial insurance broker and have a lot of carriers available in my agency.  

Technically, those sleeping over 12 built after 2016 are putting themselves in a legally liable situation if something happens as insurance companies may not cover them.

The double close or back to back closing is NOT illegal; it’s just darn hard to find a title insurer willing to do it.