@Pantelis Pantelides not sure if you found a solution but if you are out of state and looking to manage yourself but need on the ground help, a leaseing agent and using the platform hemlane is a pretty good way to go. 

Since you have a month-to-month lease, you have flexibility, so consider negotiating with the tenant or transitioning to a non-Section 8 tenant.

@Bobbie Russell  add a utility cap to the furnished lease.

I don't know if padsplit operates over there, but if not just put the rooms on zillow, and FB marketplace and screen/meet every applicant and have them sign a standard lease agreement. 

How would I go about finding a sober living operator that could sign for a lease?

Some cool benefits include expense tracking (per property), the Lease Indiciation Tool (helps predict the likelihood of a tenant renewing the lease giving you the chance to renew early and/or increase monthly rent if you know someone wants to renew), Tenant Communication (via their app), Maintenance Requests, Tenant Payments, and more.

I don't know that I had a true in the moment "oh this is it" or what not, but the turning point in general for me around life and real estate was probably moving into my house hack and signing the first tenant in the other unit up on a 24 month lease before my first mortgage payment was due. 

The "so what" of this is that we evict less than 0.5% of the tenants that we place.Leasing Performance: We track Days on Market for every unit and hold our leasing team accountable to strict timelines.

The property was leased quickly after renovations to qualified tenants, creating positive monthly cash flow from day one.

But you need to know what kind of lease structure they are offering.