Welcome aboard & glad to hear your moving over to what many sail boaters call the dark side.
As HopCar said, We call it -- "coming out of the darkness into the light!"
I live near you in Ventura county & maybe we can get together & discuss what your hoping to accomplish with your new direction in boating.
You definitely need to look at how your going to use the boat 90% of the time & what your end game dream is beyond the one 3,000 mile trip you mentioned about going up the west coast & then doing the trip from Seattle to South East Alaska.
We would love to hear the extent of your sailing trips experience as well.
Budget is important consideration --- of course purchase costs, but also operational costs & Fuel costs, etc. ?
BTW - HopCar is 100% right !
--- your anchor is too small, it’s the wrong kind and you don’t have enough chain.