How are you TD? I figure by now you must have completed the model of the 305 SB?
Interesting story about our old 27. The current owners had a Catalina 25 so the 27 was the typical upgrade. One of the reasons we sold the boat was the miserable storage and sleeping arrangements. These guys thought it was the hot setup, loved the boat, right up to when they tried to put stuff away and sleep on board. They figured that the ice box would make great dry storage but as all old Catalina owners know, that is a bad idea. The icebox drain back fills on starboard tack, as their's did and ruined everything inside. In any event, they put the boat up for sale after the second season and are now looking for something larger.
Not sure what we are going to do for sure. The powerboat has every feature that you could want on any boat. Plenty of storage, great sleeping arrangements, H/C pressure water, etc and so forth. It is very easy to winter store, blocking and stands are easy to deal with. All that said, what we discovered is that it will take you to your destination relatively quickly........unfortunately, there are really very few destinations that we have the time to get to. Canada is such a hassle to deal with now the trip over is not worth the effort. So it turns out that for us, at least for now, it is all about the trip, not all about the destination. The sailboats offered that trip, the powerboat does not.
At least from the standpoint of slips and storage, we have perfect setup. The one issue at the old marina was that we were limited by a relatively expensive 28' slip. Going larger involved years of waiting lists. Since we moved over to the club we upgraded to a 30' slip, then moved to a 40' slip this year so we have the option of going to a larger boat at any time. Winter storage is free no matter what size boat. Another one of the hassles at the old marina was dealing with the mast. The stepper was small and getting help was difficult. You were on your own for pulling and stepping, no professional crew to help. At the club there is still no professional help but the stepper is first rate and the other members gather to do masts, it is a great setup. So I guess we will see how things shake out. There are planty of boats for sale around here, many are bordering on junk becuase of neglect by older owners, but if you look carefully.......:)