I'm at a point where I could probably consider myself financially free now, but it would probably take me at least a year or two to properly convert everything to core cash-flowing assets. 

Typically when we talk about a "conversion" we mean when it converts from a lead (someone who has called) to a transaction.Either way the issue is likely not the data.

I am buying a primary residence, and in 2 or 3 years, converting to a rental. 

So if they converted it and rented it for 2 years and then lived in it for 3 they could exempt 3/5ths of the gain tax free.4.

If there isn’t significant equity value, I wouldn’t bother, as getting an ADU completed in this city as a royal PITA.An ADU can’t convert to condo btw. 

Thanks for the info. in maine we have added risk and weight of snow and ice. risky add more weight to aging roof. ive done both. but prefer rentals get metal roofs so no build up no replacement for 30-50 years. btw 1 inch ice equals 12 inch fresh snow.  

In your post you lay out some of the common things that lead to low returns when converting a primary residence into a rental.

Can that structure be converted to an LLC?

What works for one person may not work for another but in your case I would not be bothered by the management implications of taking on one more property that can be converted into a duplex.

My Thoughts -If Ownership is a Luxury Item then it should be very profitable to be a Landlord of Affordable HousingIt should be profitable with solid margins to Buy Slumlord Properties and Convert to Pride of Ownership RentalsIs there a Dark Downside of being a landlord in CA if > 50% of residents are tenants???