Capable swing keel trailer sailors!

[Skipper Lee]

I wonder if any CF users have gone long distances on a trailerable sailboat and would like to post a reply with your stories?
Often OPs post the question of which boat will get you here or there offshore safely. Whats the biggest,smallest to consider etc and i have never heard trailer boats in the same sentence. I have a swing keel trailer boat Balboa 27 4900 lbs disp. and am consider circumnavigating Vancouver island (OMG!) and that can get interesting in lots of capable boats at times.
I feel with good/adequate skills, careful boat prep, properly equipped and provisioned as well as proper cruising windows i believe i could get it done if not to heavily laden with way to much unneeded this and that.
As i will singlehand it i want as small a boat as possible to keep travelling and maintenance costs low and to get into tighter less accessed spots (keel up exploring). I should be able to get to say Mexico as well from Vancouver or where else??
All i ever hear is its a silly thing to consider and death is certainly eminent.
Am i crazy?
I would love for you to please share your trailerable offshore success or fail stories.
My boat was bought for and when ready will mostly be in the Okanagan Valley BC by the way so its not entirely wasted money, just inquiring for the entertaining responses.
I hope this prompts lots of posts and it will be fun reading posts about this brazen topic.
Best regards, Lee.