Interesting question. I have had nine new boats before we bought this one--more than likely it will be our last boat. I'm pushing eighty and my wife is slightly behind me but we both still like sailing. What we wanted this time was a day sailor/compact cruiser that we could play with that both of us could sail. Without revealing what we bought here is some of the criteria that we decided upon.
Had to have: Had to be a good sailor in light to medium winds (probably not going out in a storm), roller furling main and jib, up graded winches (I say for my wife but for me as well), a marine head with holding tank (old men HAVE to have this), standing head room (bending over is getting hard), one good berth for me to take a nap, a good dodger so we can stay out of the heavier winds, an open transom to get to our dinghy easily, a three bladed Max prop (I still hit the dock but now I do it with accuracy), companionway doors (I hate hatch boards), a forced hot air furnace so I can warm up, a simple stove to heat water for coffee and tea, and a Yanmar diesel (My last five boats had Yanmars and I am comfortable with them) and an autopilot (we got the X-5)
Was nice to get: a decent stereo with good enough speakers for old ears, a folding steering wheel, cockpit cushions (from this site), a nice looking boat (in our opinion), a lead keel (I didn't want to futz with keeping an iron keel in good shape--done that), a folding wheel, large size display sailing instruments, a pleasant looking interior (all cherry with nice cushions, an electric cooler to keep my ice tea cold--don't have to worry about refrigeration or ice,
A few things we got that we probably didn't need: A top of the line ICON VHF radio--probably should have gotten a hand held, a mid line GPS, again, could have used a hand held as we're not leaving the San Juan Islands, a microwave (came with the boat--haven't used it yet), a hot/cold shower--doubt if we'll use the shower). The hot water feature is nice because it gives us another five gallons of water. The boat came with an anchor locker and we have 200 feet of line and 30 feet of chain and a fortress anchor--doubt if we'll ever use them but a nice safety feature.
Two surprises, one positive and one negative. The negative first: it has more freeboard then I thought it might have so jumping down to the dock is still a problem (that is one reason we sold the previous boat). We're taller then some larger boats around us--probably why we have head room. The positive is that we have the WinchRite, a power adapter for the winches. My wife loves it and I won't go sailing without it anymore.
I switched to two Group 29 AGM batteries. Given the discussion on this site, I think it was a good thing to do.
It was a brand new boat in 2008 and it took a while to get the kinks out but for the moment it is just the right boat for the two of us.