Right now we are looking at something like a C&C 24. Something we can trailer up to the San Juan's and BC and still be able get around on our little reservoir as well. :svoilier:GOOD ON YA!!!! You are approaching it the correct way (my point of view)!
When we were looking for a boat we were working and a ways away from, and a long time from casting off. We thought over the idea of a larger (40 +/-) boat, but were inland at the time. We were worried about getting it to the sea if I was laid off. We thought about a small trailer sailor. but if we got laid off we would not be able to finance a larger boat without a job. :|
We settled on a trailer-able boat that could also circumnavigate. Worked GREAT for us. So far we have sailed lakes, the west coast Seattle, then from the San Francisco Bay area down through the Sea of Cortes and mainland Mexico. We have trailed back to the Bay area, then to New Orleans (and returned to the Phoenix area a few times) and sailed the West coast of Florida. Getting ready to head out to the Bahamas soon.
A side note, we have had 4 serious offers to trade straight across for boats from 36 to 41 Ft. STILL love our boat. You can see some of our adventures on our WEB pages and Youtube pages. And 5 DVD that are for sale.
DO IT with a plan!! :cut_out_animated_em