I'd look at both.
We bought our boat through Bruce Hill this past August. They were very easy to work with and coordinated it so that we had several hours on the boat with the sellers at the time of closing.
FWIW, the O'Day is not priced too outrageously based on a simple search on yachtworld: O'day 322 boats for sale - www.yachtworld.com
Finally, I watch the craigslist boat ads for our area. Here's one that might fit your criteria: 1988 Catalina Sailboat 30'
(although that's quite the head sail!)