Jack,Buy a fully loaded boat and I don't think you will regret it. The wheel steering is a must for me and opens up the cockpit. The marine head is nice, but a very cramped space. I don't have the bimini, but will order one for the next season and consider getting a custom dodger and a connecting canvas piece. I bought my boat used (one season old) and by the time I add the missing options and some extras, I could have bought new. New 2006 Hunter 25's are currently selling in NJ for about $5K below list.The 25 is not that big a boat and I don't think it will be too much bigger than your O'Day. However, I like the 25, but I don't overnight on it, keep it in a slip and daysail only. The Hunter 260 is one of the biggest trailerables (water ballast), has a cabin as big as a 27 footer and carries a lot of sail. They aren't built anymore (last year 2005, I think), but worth a look if you want to consider a water ballast boat. If I had to do it again I would get an outboard with a power tilt optiion. I don't like the Nissan 9.8's tilt mechanism. Also, the boat steers very poorly without the motor connected to the rudder, so buy or build a steering linkage to connect the motor to the rudder under power. Not a big deal but steering improves 1000%.Barry