It's great that condition is a primary driver for you. A lot of first time buyers (including myself when I bought my first boat) focus a bit too much on price and don't give enough consideration to condition. Catching a boat up on 5 or 10 years of deferred maintenance isn't cheap, even in this smaller size range.
Originally Posted by Sheppyb
We will see where things go over the next few months. With regards to the specific comments on the Westerly, I do appreciate being candid. Now all I have to do is to try to sort out those statements with others of equal experience that say things contrary.
I'd give Jeff_H's comments more strength than almost any forum member on any of the sailing forums that I read. He provides a lot of great information on here and I learn something from almost every post of his that I read. If you read his other posts I think you'll find the same to be true for you. If he says a boat is a dog I have to believe that it is a dog.
25-29' is a big size range, especially if you plan on doing any cruising. I started with a Catalina 25 and found it a little tight for two for cruising longer than a weekend or two. I moved up to a Pearson 28 which is at the upper end of your scale and it is a lot more comfortable. On the other hand the Catalina was a lot cheaper to maintain and had many fewer systems, which made it a great first boat.