Newer boat vs older in same price range

[icedog11]

I'm making my first post and I'm really nervous about asking a stupid question. I have been doing my home work, and feel I'm really sold on Island Packet in the high 30's to mid 40 foot range or a much older Hinckley Bermuda MkIII around the same length. Prices are really very close. Is the upgrade in original manufacturing offset by the modern build of a boat built in 2005 vs. one built 1987-89. Both boats seem to fill the needs I have for a live aboard, and blue water capability. My curiosity lies in the difference in build quality that has developed over the two decade difference in the boats.