Passage from Alaska to CR
I'm not sure if you're still reading replies to your post, but most folks are warning you not to do this passage relying on your outboard. The reality is that even the best engine is not as reliable as a good set of sails and some skills.
You seem to be concerned about not knowing how to sail-- well it's not that hard to learn the basics -and you will always be learning after that.
Like you, I was a complete newbie to sailing a little over a year ago (though with lots of ocean and big lake experience in a sea-kayak)- I bought a 1982 PSC Flicka (after years of dreaming about it) took a one week course at the Chapman school in the spring of '08 and then sailed my boat from Florida to Vermont over a 5 week period last June/July '08. My crew for most of the passage (my 23 year old son) had never sailed.
We both learned as we cruised (mostly on the ICW) -- and I was sure glad that I had a good boat and good sails and "some" skills - since the bulk of my problems were with the engine (inboard diesel).
I don't know much about your boat or sailing from AK to Costa Rica, but assume you can run the inside passage most of the way to Vancouver or the San Juans- and get to know the boat as well as work on developing skills before you need to run too far offshore.
So my suggestion- don't give up- but take an ASA or equivalent keel boat cruising course before you set off. Then take it one day at time and see how you and the boat hold up to the challenges.
I know that the class gave me the confidence to try sailing rather than shipping my boat north, and I am sure glad that I did it. Sailing (and learning my way around a diesel engine) has become a big part of my life (and my wife's) and we are planning some long passages (blue-water) in the near future. Meanwhile, we get out there and sail in all sorts of weather to build skills-- and have fun.
Hope this helps-