I have a couple of suggestions that you could explore. There are two revenue generating startups emerging from Y-Combinator this year, (http://www.tipjoy.com/ , http://snaptalent.com/ ) I believe both have great potential! Here is the descriptions ala techcrunch (http://www.techcrunch.com/2008/03/14/y-combinator-demo-day-roundup-for-spring-2008/):
Tipjoy is an easy micropayment system for the web. It has been designed to cut out the steps necessary for website visitors to leave small amounts of money for content publishers, such as bloggers. The Tipjoy button placed on a website asks for only an email address and by default registers a donation of 10 cents. The service is nearing 70,000 impressions per day and the founders are exploring different models for micropayments, such as employing them to finance high definition video on the web.
Snaptalent is an advertising network for job listings that uses IP detection to determine whether website viewers work or study at particular companies or institutions. It then displays listings from employers who want to attract workers from organizations known for their talent, such as Facebook or Harvard.
I believe Snaptalent would have more benefit to the growing Portland startup scene, by providing both an avenue to promote local startup jobs and find local talent.