Write every single expense down.

.-- I have some skills in remodeling/construction and some vacation time I could take to do more major repairs/upgrade/etc.The main goal I'm looking for advice is how to go from being a single family house hacker to owning a commercial real estate space that I could art studio hack (share loan payments with other tenants that I manage) to use as a shared art / video /dance studio? 

The unit is occupied by an unemployed single female on section 8 assistance.

You could also pass any credits to a single investor however you must meet other complex partnership provisions such as liquidating in accordance with capital accounts, DRO, etc. 

I'm focusing on single family deals with a buy and hold plan.

I do for sure have sperate personal and business accounts...this is a must; however, I do pay multiple property bills from a single business account...tracking it is just a matter of creating property categories eg 123mainst:Electric, 123Mainst:Taxes, 456AppleSt:Electric..).  

What is the hight limit on Single-Family Dwellings in Venice, CA?

It would probably also work better if you were buying a single family home, because that would pull more on the "aww how sweet" part of someone's brain than moving a family into a 4plex.

If the property is a single story, and joined to just 1 other property, it is then a Villa.

I currently have in the making a package deal for 143 single family homes in Mesquite.