But I see myself in the same shoes as @Oscar Moncada.

Having your own source/relations are much more comfortable to me, I will definitely contact her.

If you think you'll only do it say, 5 times, then wouldn't you be better off (comfort-wise) just renting out the non-rehab rooms while living/rehabbing inside, which is sustainable?

I may eventually consider investing in a long distance market, but I think I'd like to get my feet wet locally so I get comfortable with the process in a place where I have more resources and access.Does anyone have any suggestions on what markets in the general Portland area can potentially provide cash flow through single family rentals?

I would be comfortable trying software with just a few vanilla rentals. 

@Kelsey Mortimore find deals that you are comfortable with, even if there is a drop in RE prices. 

If you are selling to another investor, they just step into your shoes. 

Usually that comes at a price of a lower commission split. 80/20, 70/30 or even less % to you until you feel comfortable.

I kept the addendum I used and just added a couple sentences that made tenant comfortable while still protecting me.

However, I quickly realized (with the help of my wife) that before we could comfortably start investing in real estate, we needed to make some significant lifestyle changes.