It depends on what you are looking for. From Portland, all of the local skiing is on Mt. Hood. Mt. Hood Meadows has the most varied terrain and is the largest of the Mt. Hood ski areas but not a lot of steep or gnarly terrain. Ski Bowl is the closest to Portland and actually probably has the best expert terrain. However, it has the lowest elevation and can get less snow and even rain while the other places get snow. Lastly, is Timberline. Beautiful WPA lodge but with mostly cruiser runs. If you are a boarder, they have a fairly large terrain park area.
If you can go on a weekday there will be no crowds/liftlines at any of them. If you have to go on the weekend, they will all be crowded. All three have some form of night skiing.