I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.

Typically speaking 20% down (80% LTV) is the bare minimum that commercial lending requires.  10% down is unheard of unless you are getting a great deal and negotiate some small seller financing in second position or getting an SBA Loan for acquisition where your business will occupy over 51% of. 

Lenders will allow parents to be a non-occupying co-borrower on a home your college student plans to live in.

The down payment on owner occupied properties can be as little as 3% on owner occupied properties.

This is an essential tool for anyone buying a tenant-occupied property. 

Assumption by an EntityUnfortunately, assuming a VA loan directly through a legal entity (such as an LLC, corporation, or trust) is typically not allowed because:Primary Residence Requirement: VA loans are designed for owner-occupied properties, meaning the assuming borrower must intend to live in the property as their primary residence.Credit Review: The VA and lender require the assuming party to undergo a personal credit and income review to ensure repayment ability, which entities cannot satisfy.3.

But usually for a tenant occupied it's like $90-120 per monthI've noticed a lot of multi-family buildings are pre-WWII housing inventory - are there restrictions or issues common with that (historic districts, crazy high utility costs, etc)?

You can get more than one VA loan depending on your allotment and you don't need to owner-occupy the second one so I would look into that first.

Both occupied and cash flowing. 

They dont want anybody other than condo owner to occupy the property.