As long as the set back rules aren't ridiculous and as long as you don't run into any solar access issues, you can easily build a home with appropriately sized garage on 2700 sf.

The one for 1100 was not updated, old brown paneling and such...but it did have a garage where ours does not.

In Seattle the requirements for a separate panel in each unit, usually separate electric meters, separate heat sources, separate hot water heaters and plumbing runs, etc make legalizing a non-conforming unit pretty expensive.

They installed a new electrical panel and rewired I think 2 of the rooms already.

I think the opportunity, especially in the bigger units, is to slowly have the tenants pay the utilities and/or convert to solar, energy efficient, water efficient for common areas.

I love paint on wood paneling.  

It looks like you have some 5 panel doors with original two part trim then some basic doors in other parts of the house.

A possible monthly meeting agenda could be a "Note Panel".  

It can be a very complex process or a very simple one depending on how the power runs to the individual units from the main panel on each building.Once the meters are in that's when you would engage a utility billing company. 

Also, I'll be moderating a panel discuss on Saturday at the Papersource event in April, so please be sure to connect with me.Bob