For me with my limited time, limited funds and limited boat knowledge....
Dealbreakers:
Any delamination

(for that matter it would be a dealbreaker for me with unlimited time.....just not worth it).
Problems with spars.
Non-functioning engine.
Major concerns:
standing rigging issues,
engine issues (assuming usable but needing more than routine maintanence).
osmotic blisters ( I understand this is a form of delamination, but minor issues that I feel could be solved on next haulout wouldn't be a dealbreaker)
Unusable sails
Unsafe electrical systems
Minor concerns:
What makes me think I can afford this or any boat
Okay pretty much everything else, running rigging, cosmetic blisters, canvas condition...etc...
BTW Dawg, Thanks for starting this post, great info,
Michael