Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

The fideicomiso or bank trust, whereby the title is in the name of the bank but they don't lease the property to you; you're the owner for all intents and purposes.

What are the comparables in your market doing at your expected price point?

Getting right to the purpose of my post, with all the relevant context: I’m 52 and living near Seattle.

The cost associated with insurance for not having 20% is peanuts compared to what you potentially can do leveraging your down payment. 

You could, for the purposes of verifying that you are not renting to someone who is potentially dangerous or financially incapable of shouldering the burden of being a roommate, ask them to apply through Zillow so that you can see their background check, that also gives you the opportunity to have others who might be interested in being your roommate as well, apply.

This is a beautiful house - rehabbed/looking new and fresh - walking distance to the water etc, yet low gross yield  compared to Byrd (???)

This creates a market for both short-term and long-term rental properties.Affordable housing, Compared to cities like New York, Washington D.C., or Boston, Philadelphia offers relatively affordable rent, or section 8 tenants, especially those who are relocating from more expensive areas. 

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

I'd like to know your thoughts/advice on how to compare long-term and mid-term rentals.