Riverdude,
I've been in both. The 27 has more freeboard and cuts through the waves to Catalina with no problem. You can actually sit up in the cuddy of a 27. No way in the 29. For pleasure boating, the 27 is a good choice, if you want to use the cuddy. To cut across the waves at WOT, size does matter and the 29 is better.
Jim