I like to follow the gossipy openings and closings of the Portland restaurant scene as much as anyone, but it's not all that often I have the cash to throw at getting the proper experience at these mostly fancy joints. That's the whole point of Portland Dining Month, which is March! Soon!
The deal is that 100 Portland restaurants will offer up three courses (app, entree, dessert) for $29 (many of them will accommodate vegetarian, vegan, and gluten-free diets, too), to make it a bit easier for you to participate in the restaurant culture that so influences the city's reputation.
Additionally, they're running a contest on the Downtown Portland Facebook page starting March 1 and through the month wherein you can win "dinner for two for a year," which translates into over $4,000 in restaurant GCs. There's also a charity aspect: For every reservation made on the web site, Downtown Portland will make a donation to Oregon Food Bank. And don't let the "downtown" stuff throw you off—this is a citywide shindig and the options are vast, so you may want to start mapping your strategy.