There is much to consider:
*Sailing performance
*Cruising ability
*Construction and groundings
Sailing Performance - On sailing performance I'd love a deep fin with bulb (but never protruding forward of the blade).
Cruising Ability - We cruise and like to gunk-hole so our longer shoal-ish fin gives us a good compromise and we can still outpoint many boats with deeper draft. When I am cruising I love my shoal-ish draft but when going up wind I always wish it could be deeper.
Construction - Lead is the only material I will consider. You simply could not pay me to own a boat with an iron keel. External bolt on is also my preference and if done correctly brick $hit house strong. I am not a fan of keel centerboards, my family owned KCB boats and I have had too many customers wind up with massive repair bills on aging boards. My uncle had his cable snap then he hit a ledge trying to get into the cove with a 11' draft, drifted backwards on it and drove the board up though the cabin sole. Even my customer with a large Alden, a beautifully constructed boat, had to do major surgery including custom made gears, pin etc. far too soon in the boats life.
I won't personally buy boats with:
Keel-Centerboards
Encapsulated ballast
Iron keels
I have owned a wing and won't likely go that route again unless everything else about the boat is spot on..
Groundings - Again here my preference is for external bolt on lead. Why? Have you ever seen a boat with internal encapsulated ballast that has t-boned a solid granite Maine ledge? That is your answer. It takes MONTHS and MONTHS and MONTHS to properly dry out an encapsulated ballast before a proper repair can be made. When they are incorrectly "patched up" they freeze and split. Very, very few boats with encapsulated ballast are built correctly enough to warrant a meeting with a solid granite ledge.
After over 45 years of sailing around New England and Maritime granite, watching groundings, repairing grounding damage etc.. that is where I land...