Does that really help with my 2 main issues?

As it stands now, I am going to renovate the apartments, the tenants will pay me and I will communicate with them directly about all issues with the property etc.

The main issue that would scare away buyers is that there is a lot of debris (couches, household contents, ect.) that have been basically thrown in a pile in the front of the house.

(Oregon Landlord Tenant Law prohibits a seller from giving the tenant a vacate notice for a buyer to move in.

I don't think rental arbitrage was considered when the relevant tax law and guidance was written, so it may be an area of uncertainty. 

The only thing missing is action.You'll learn 20x more by taking action than by reading a book or listening to a podcast which are always general knowledge that gets repeated over and over.Once you dive in you will start to come across specific issues and problems you didn't even know existed!

I'm looking at the protocol to register and then have the safety and lead risk inspections, fix any issues and ultimately get the certificate of compliance for 3 years, then repeat.

Insurance doesn't cover maintenance related issues or "wear and tear."

Also, if you haven't already, make sure zoning laws allow for that use, and that there is no code provision that prohibits a certain number of unrelated individuals to live in a single residence.

The biggest issue we are running into at the moment is finding a profitable multi-family unit and how to fund it.