We lived aboard and cruised on a Westsail 32 for 4 years. Had all the living space and storage
we needed. Of course, the W32 is a BIG 32' boat. You could find one outfitted to the hilt for under $50,000. We averaged 118nm per day with virtually no engine
usage with a max day of 176nm.
Someone on this site is offering a ready to go Alajuela 38 for around $60,000. http://www.cruisersforum.com/forums/...ng-158033.html
The Alajuela is an Atkins Ingrid that has been optimized for sailing ability.
There are an awfully lot of boats out there under 38' and $50,000 that would make good cruising boats
Windward ability is something that is greatly over rated when it comes to cruising. Unless you are a masochist, you'll spend almost no time hard on the wind
. The World Cruising routes are almost exclusively reaching and running.