In the Portland area, buy a good used Ranger 20 or Cal 20. Join the active local fleet. Race it at least one evening a week all summer and fall. You can do this for less than the cost of one new head sail on any 35 footer.
You will learn more about boat handling and sailing, in one season, this way than you would pottering about in a big boat for the next nine years.
Then resell your small cruiser in a couple years and get something larger. By then you will know a lot more about sailing and about yourselves.
Get out on the water.... get a bunch of "tiller time."
You'll have a lot of fun, too!
We started out in an R-20, and ended up racing and cruising it for five years. Then a 26 foot boat for a decade, and our present 34 footer for the last 15 years. Sisterships to ours have done many Hawaii trips.
It's good to do your research and spend some time on the WWW, but what matters most is..... time spent under sail on a responsive boat.
My .02 worth,