I don't think making this a nice remodel is going to help since you're likely not attracting the caliber tenants that's willing to pay more for something nicer... that tenant is looking to live in this area.Now, if you went the Section 8 route you might be able to push to the $1,300 - $1,400/mo range.

I live in western washington. 

Are you looking to house hack by living in one unit and renting out the others?

I do pretty decent for my age, and I live at home still, so I've been saving up a lot of money.

What is the quickest and most feasible way to transition from living there to setting up this house for passive income: leaving a property manager or somebody to take care of it!

Recently I bought a home as I am bringing my parent to live with us we just need a more space.

You can also contact a local alcoholics anonymous or other organizations and let them know you have space available for anyone living sober.

This tenant currently lives in my property with a roommate and they are both equally responsible for the rent.

Not quite, Baltimore has been my major focus for now.I actually live around Edgewood though!

There's always gonna be poor people and those poor people are always gonna need a place to live.