(Who cares about living for free, you aren’t doing that now.)

It is common for a GC to bid higher on a job that they don't really want - either because of location, type of job, or sometimes the personality of the client :-)Then if you get the job, you're happy because you are making a lot more profit.... and if you don't get it, you don't really care because you didn't want it anyway. 

I plan to move in after purchase and live there as my primary residence.

A little about me, I was born, raised and still reside inSan Diego CA.

Intent to build and use as a primary residence?

If used for 15 days or more or 10% of the rental days at fair market value, it becomes a residence, subject to specific regulations.

For one thing,  my lease does state that the property manager can adopt rules and regulations for the benefit of residents and the building.  

Ideally, properties should have separate entrances for the main living area and the ADU, providing privacy.Kitchen and bathroom facilities should be easily modified or expanded to accommodate both the main residence and rental space.

Same with landscaping and yard care.

I'm searching for an insurance professional to discuss the concept of negotiating group purchasing property insurance for a discount (similar to what is done through health care via employers).Are there regulations that would make this prohibitively difficult in the property insurance industry?