The landlord could offer to mow the lawn and shovel the walk, while making the tenant responsible for repairing or replacing the washing machine.Landlords and tenants need to confirm what is required within their written agreement.

Water heater 12 years to replacement (may need some service before replacement).Recognize many cap ex items are years away.  

This sounds like a good idea. 

for example when changing cabinets, addressing trim, door pulls. hot water tank replacement: place a pan under it.  

Hey @Aubrey Adams - not to sound blunt, but there is no good time to buy.

Also, it sounds like you are in a great time of life to rent to roommates - I don't think you would regret figuring out a way to do some sort of house hack like that right now!  

It doesn't sound like you actually have an illegal unit here.... you have a two unit with a garden.

The HOA takes care of everything outside of the studs and I save enough to just replace anything that breaks and skip the repairs. 

Trying to manage a $1M Airbnb rental while it sounds good you got $6500 in bookings you still have significant costs to operate it with maintenance repairs, utilities etc.

Sounds good to me, I'm always happy to share my workflow with others and making connections.