I have 8 separate 5 yr fixed rate mortgages (and P.notes) that the same bank (in Wisconsin) has made to two of my LLC's and secured each loan on a separate property. 

I bought the property, did a lot split to separate the duplexes and refinanced and saved a lot of $ long term with no downside in rising interest rates when the loan comes back up for it's reset.

Should I add the other unit as a separate asset and take depreciation starting from 01/01/2020 - Date of Conversion (as I moved out in December 2019)?

San Diego does not allow renting a JADU as a separate unit unless the primary unit is owner occupied.  

Are you planning on waiving escrow (paying taxes and insurance separately from your mortgage payment)?

The house has an attached ADU (separate entrance and garage in the back) that I may keep for myself or a long term renter.

I am tired of having two separate records.

But the contractor still charged me for ad hoc things he had to buy during the work since I said I am paying for the material separately. 

Someone convinces you to separate yourself from your money, you then give it to someone who charges you a fee to manage the money, but the only managing that's done is sticking it in a "diversified" fund of some sort.

Ideally it would be free, and would allow multiple categories so I could separate my two business, healthcare, and personal.