Your original post was rather brief, and certainly qualified available service we can all agree is an important factor.
However, having said that, how do you plan to use your boat? In a destination versus journey world of boating, the 27 Classic is a journey boat, and definitely the 27-OB is a destination boat. Are your bodies of water relatively small lakes? Do you have children for water sports (tubing or skiing) that only the 27-OB can accommodate?
Both of these boats overnight very well, and are trailerable. The Classic is more fuel efficient and the OB offers more bells and whistles. You can find both boats in the used boat market but only the OB new, if that's important.
Figure out how you plan to use the boat and you've answered most of your questions. Good luck in your decision making!
Bob
The Doghouse 2