I was going to stay a couple nights with my family there over fall break and the nightly rates seem really crazy, between $300 and $900 for a typical rental house.

The bottom line is that if you bought your properties at the judicial sale (usually in the fall), the non municipal liens are cleared by the sale.

With you not being there you're just going to need to make sure all the things you were doing and managing don't fall by the side. 

This is a mistake a lot of new investors fall into. 

Normal wear and tear refers to deterioration over time from ordinary use, but damage like a large oil stain in the driveway from a vehicle is preventable and would fall under tenant responsibility.

This includes medical malpractice and auto accidents, both of which are significantly higher than what you would see with a landlord slip-and-fall or mold injury claim.3.

The three properties referenced above: a) one turns into a mid-term allowing me to get higher than normal rents that cover everything; b) one turns into a short term; c) the third I focus on getting the highest dollar with short fall of may $100 per month and planning to raise rents in the next few years to cover that eventually.Problems: I have been a long time airbnb user.

I am looking to purchase a property that falls under the minimum limit for DSCR but qualifies for a conventional loan. 

The majority of STR properties in Oregon fall within the loan limits of  up to $2-3M depending on the property type.

Make sure you have multiple exits to fall back on if the investment doesn't go as planned.