Our real estate agent did a video walkthrough for us of the units (one vacant and one occupied -- don't worry, for the occupied she handed her phone to the tenant for them to do the walkthrough).We're gonna work with our agent to answer the following concerns, but I wanted to see what you all recommended as well:1) We drove past the house and looked at it from the outside, but my wife is uncomfortable purchasing a house for us to live in where we haven't seen the inside, even if it's just the vacant unit.

Most of the routine payments and receipts are handled by auto pay.

I want to provide a safe environment for my tenants and don’t want anyone to feel uncomfortable.

What do you all think about this; Would you live in an uncomfortable situation to make a deal work?

I think you can definitely get a multifamily home to house hack in the Portland area, it really just depends on how uncomfortable you are willing to be & creative thinking. 

Like when you call to these people you don't know, one thing youd like to do is to be natural and honest but I don't know if I'm allowed to tell the truth about where I'm calling from when they asked and it actually makes me uncomfortable sometimes because I do not know what to say and your words here gives me light.  

In our market we routinely see plane loads of tourists from China and Japan in the summer months.

It will be awkward/uncomfortable, but arrange a sit down and explain it's best if she leaves without getting attorneys involved as that will affect her future rental aspects.   

I have properties outside Loop 610 and they have been great to me.You mentioned that you are uncomfortable with networking, then I have to challenge again. 

VRBO and Airbnb platforms make it pretty easy to self manage.Find a great cleaning company that can handle turnovers and be your eyes and ears and a handyman for small repairs and you are pretty much there.You can use sites like TAKL.com to find other services that you don't routinely need.