Well, my must haves are (rated equally), excellent sailing characteristics, safe and solid, and comfortable for living.
To meet the first requirement my boat must have good performance including to windward, lots of sail area, deep keel
, big winches easy to operate, lines led well for easy handling and not too much friction, good visability forward, responsive to the rudder
, easy to reef, a clear foredeck, and a windvane
. Its a sailboat and I like sailing or I wouldn't be out here, so make sure it can really sail.
: strong construction, good rig, clear decks and cockpit
so you can see and so heavy weather
dosn't make it dangerous to move around on, good ground tackle and lots of redundcancy omn everything, good motor
and drive train, life raft (inspected) ais
and a charting system with a big screen
For comfort: comfortable places to sit and read with good lights, good bed
and good sea bunks, good ventillation, simple refer but some freezing capacity is a must, big tanks
, good watermaker
, lots of storage
, a place to work on stuff without using the salon
table, good spray dodger
stove on gimbles, good music
system, heat or airconditioning depending on where you might be living.
And on top of all that, try to keep it simple. the more complexity you have the more time (and money) you will spend fixing it.