Worst case scenario we pay more for housing than we are currently but would be able to get by, best case we would have a very good investment property.

Sometimes the people you think you want out the worst end up having another tenant trump them with worst habits or worst payment history.

Worst house on the block in a good area.

The worst that would happen to the property owner is they would be foreclosed on and the city wants to protect the most vulnerable population.I can't blame you for investing outside of Portland. 

Sell now because the economy is getting worst every day.

A clogged gutter/downspout can cause water to avalanche over and go into the foundation.  

This isn't an office job, where the worst your have to worry about is a jagged paper cut.

I am kind of trained to expect the worst at this point!!

Not great but getting 2% interest per month isn't the worst thing if the owner comes to redeem. 

If your inspector is unable to inspect I would assume the worst and offer accordingly, or find another property.