How live-aboard-friendly is Newport OR? I'd say that's the first part of the puzzle. It's difficult to find legal live aboard moorage in Vancouver BC.. and if you do it's pricey and the city gets its share too. As a result, esp if financing the boat it's not a particularly inexpensive way to live.
As to the boat itself, both approaches may well work for you... how much use you'd get out of the larger liveaboard may depend on how easily handled she is, and what's actually involved in getting away from the dock... A disadvantage to that part of the coast is a lack of protected cruising waters such as what we enjoy in BC.
It may be that an inexpensive trailerable, continuing to live economically in your trailer, and getting sailing experience by traveling around to different areas (including Puget Sound and BC waters) makes the most sense.
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)