Ok so imagine you are building your skills on a 25ft Catamaran around Sydney.. Something like a Beach Marine Macro 25 perhaps... And "your" ambition is to be island hopping in the south pacific 10 years from now. You know that the Macro 25 will not be suitable for more than a short trip to Sydney harbour or perhaps Newcastle. So you are thinking forward a few years and eyeing off a switch to a blue water cruiser and of course you want this choice to be a long term one. But the choices are innumerate. There seems to be a million designs and variants. But you have a few parameters to work with:

In the 38-42ft range.
In the price bracket of $90 - $120k. (puts a big cat out of reach)
Your preference is a younger boat, so late 90's would be ideal.
Speed is always important
Shorthanded will happen so a furling main would be great but in mast furling sounds bad. What about in-boom furling?
Horseshoe galley rather than open style?

Now the key ingredient. what type of sailing vessel are you thinking?

Centre Cockpit?
Creates an amazing aft berth for keeping the missus happy
Hunter 42ft; $120k; 1997
www.boatsales.com.au/boats/details/1997-HUNTER-42-CENTRE-COCKPIT/SSE-AD-5702340/

North Shore 38?
A classic; Ticks most boxes and leaves budget for more cruising
$82k; 1988;
www.boatsales.com.au/boats/details/1988-NORTHSHORE-38/OAG-AD-16452785/

Glossy Euro Cruisers
They look like heaven; but does the cruising reality stack up??
Bavaria 40ft; $120k; 2001 www.boatsales.com.au/boats/details/2001-BAVARIA-40-CRUISER/OAG-AD-16528729/
Beneteau; 47ft; $106k; 1998: www.boatsales.com.au/boats/details/1998-Beneteau-Oceanis-461/SSE-AD-5391981/
Jeanneau; 40ft; 119k; 1999 http://www.boatsales.com.au/boats/details/1999-JEANNEAU-SUN-ODYSSEY-40/OAG-AD-16033088/

Pilothouse?
Keeps everyone warm and dry on the off days when nobody wants to be in the weather

Ketch?
Centre cockpit, shorthanded? Speedy?
Problem; most seem to be older or out of the price range.