Re: Cal 27 T2 Doghouse for a rookie?
As with any boat of that vintage you need to be on the lookout for wet deck coring, mold/mildew in compartments and bilges that might indicate some neglect, the rigging is likely on its last legs unless you have access to records indicating otherwise. It's bound to need a little TLC unless it's been looked after by a meticulous owner.
Asking prices seem to run from hundreds to $10-11K depending on region and condition. Something in the 4-6K range seems more likely, and then only if it's pristine (depending on power).
As I recall they sail pretty well, we had one up here that cleaned up on the race courses in the 80s.. she was quick and well sailed.
It's on the small side for an Alaska trip, but that mostly depends on your own tolerance and 'comfort needs' once the boat is brought up to condition to do the trip.
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)