I also learned to sail on the Columbia. I lived in Portland my entire life until I moved up here 7 years ago. Back then there wasn't very much in the way of guides to cruising the river, so I went out and created a video called "Cruising the Columbia River - Vol. 1". It covered all the marinas, parks, docks, and fuel docks from the mouth of the Columbia to Bonneville Dam. This was around 2001, so it was made as a VHS. I still have quite a few left, so PM me if you would like one.
Anyway, yes you can cruise from the Pacific Ocean all the way up the Columbia and Snake Rivers (locking through 8 dams/locks on the way) to Idaho! It's supposed to be an awesome trip. As far as skill level, just like Bryan said, the river can throw some nasty wind, waves, and current at you. Especially in the Gorge. I bought a Gulf 40 in Hood River and brought it down to Portland, and the PO said the worst green water he encountered in his 5 years of owning the boat (including two trips to Alaska and back) was in the Gorge! So it would be prudent to be somewhat experienced, and to have hiding holes/places to get out of bad weather known at all times - especially in the more remote areas of the Snake River.
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"Always approach the dock at the speed you wish to hit it."
1978 North Sea 33 Pilothouse Cutter (Ta Chiao)