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Mike...I guess I will play the fuddy duddy here.
I would not consider any mid-30-40' range boat from the big three for a trip with family down the Oregon coast which can be simply treacherous and with nowhere to run for safety. I also don't consider the Columbia River a great place to learn to sail. If you want to learn to sail and cruise, I would get something up around Seattle that you can really USE in relatively protected waters that can be increasingly challenging as you are ready. Anything you choose would be fine for that area.
There is nothing magical about living aboard at a dock. Indeed it is not much fun on a relatively small boat with a family. What is fun is living aboard and cruising...regardless of the space.
When you are ready for your cruise...take whatever you bought for Seattle and truck her south or sell her and buy something suitable to your cruising dream. You don't need anything special to do the gulf, the East Cost, ICW or Bahamas.
To my mind...the biggest problem you have is wanting to live aboard in Portland while learning enough to go cruising. I think you have to pick one or the other.
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