Both occupied and cash flowing. 

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)?

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

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.

One unit is occupied by a low-income senior not on the Housing Choice Voucher program and paying well below market rent.

Two reasons could be renovations or the need to personally occupy the unit.

i mowed the lawn myself.and if you think about owning a rental long term - ideally it will always be occupied. 

To learn more about which one may be best for you, feel free to send me a private message.Old Town North: An Unused Eye Soar Transforming into a 2.5 Million Square Foot Community CenterThe GenOn coal power plant, which opened in 1949 and was shut down in 2012 due to concerns by residents about local pollution, has occupied an unused 20-acre lot in Old Town North for the last 12 years.

My girlfriend and I occupy one of the bedrooms in the home.