I would highly recommend checking out Hawaii
on your way.
Many, many folks buy a boat on the west coast
and set off on their dream adventure, only to find after a couple of thousand miles of sailing, they (or the wife) hate it.
Boats there can be many thousands of dollars cheaper than normal because they are so far from large markets.
As to what;
I cannot stress enough that it is NOT important if you like the looks of a boat. If you are serious about sailing to far off places, you must have a boat that fits your needs.
Make a list of what you'd like in a boat, what you want in a boat and what you must have in a boat; then find the boat that has the most of all the above, including looks, but really, can you see your boat when you are sailing?
Foe instance for me, it was 5 things;
1) roller everything, main, jibs and mizzen if it had one.
main winches, remember, I'm 65 & had no sailing partner.
3) a real, centerline queen bed
; you are only sailing 5-10% of the time
4) a stand up or at least, walk around engine
room; I'm tired of crawling around on my hands & knees
5) a bridge w/ inside steering
as well, for inclement weather
I didn't get the bridge or inside steering
, so sad.
But, I got 4 out of 5 and in boats, that's pretty good.
Hope this helps.