Consider doing more investing the boat you want to do that voyage in. You might trade
off size for cost and get a stout boat.
Then, no matter which boat you decide on, try going down the west coast
on gradually longer runs to build up your skill set. It would be much easier to hire a skipper
for a two day run than a crossing.
Then on the run, don't let the skipper do anything (well almost nothing), have him tell you what to do and why you need to do it. Be very outright when you are hiring the captain
and you should be able to find one willing to help.
If you are going to be the captain
, BE THE CAPTAIN! Don't give your power to some one else. It will be your boat and your life, don't cut corners to try to rush it!
Just my 2 cents...