Be honest about your history and abilities. 

You need to have the ability to contact previous landlord to verify previous rental history.

You could also add a clause about your ability to terminate the lease if they cause problems in the neighborhood, don't cut the grass, etc.

All units would be metered so data would be there to bill the tenants (so no ability to question the bill) but landlord would still pay the bill given we can not have 4 main master water meters (can only do 2 x1 master meter + x1 sub meter combinations). 

Some weird guy is yelling from the side about bowling......

Also if this property is on septic that also can throw a wrench into the ability to call a space "a bedroom" as septic systems are sized and permitted based on the bedrooms.

I would just continue to grind over the years until you have the ability to pay for the DP yourself. 

(May also cut significantly into the current cash flow on it)I know you mentioned not doing a HELOC on my primary, but wouldn't it be advantageous to have the ability to pay off the line of credit instead of be stuck in a payment that is much higher? 

With the city contemplating expanding the ADU ability to city wide, is there any benefit to doing a rezoning now (assuming successful) before the citywide expansion takes place?

You'll want to 'screen' a few (or a lot) until you feel comfortable enough to know which ones you want to work with, trust, and feel have the ability to 'take you to the promised land'.