One thing you didn't mention is what is more important, speed or economy. If you're retired and want to be taking longer leasurely trips, a diesel powered troller displacement hull or power cruiser sail boat will have a much longer range, and suck much less fuel running at 6-7 knots, vs a planing hull running 20-25 knots. What's more important, getting there quick, or enjoying the trip.
There is also a quantum leap in purchase and operating cost between a 22-24' cabin cruiser and a 26-28 foot, ie the double the cost of the boat, and double the fuel consumption. A 26-28' cruiser at today's fuel prices sucks upwards of 10 gallons an hour, so you can easily burn $200-250 per day.
