I have posted the back story a few times...
In essence, before we married we discussed non-negotiable things. She didn't want to have kids and I wanted to sail and would own a boat at some point. A few years later my Cousin Mike passed away in his mid forties from cancer. I realized that waiting to sail just wasn't an option for me anymore. I got tempted to bid on a boat on that devil program ebay (which led to an embarrassing track record of other impulse bids...but that is another story) which was for sale by a local sailing club that I actually belonged to at the time. That is how I ended up with my Lancer 25.
Mentally I made a deal with myself at the time. The deal was that if I couldn't bring the Lancer back from its slumber...it had been sitting for about 2-3 years...then I really didn't deserve to risk spending a lot more money on a bigger boat. By the time the trailer discussion occurred I have had the Lancer for over three years. It was a maxi-trailerable with little head room and a broad shallow keel that made it slow and unresponsive. Still, I was feeling guilty about the $1500 winter storage year after year and the trailer was my solution to that.
So...at that point my reasoning was (a) that I had met my mental goal with the Lancer (b) I really could afford to spend at least $10K on a boat (c) the Lancer really was frustrating me because it sailed like crap (d) I am 6' tall and wanted to pee standing up and most importantly (e) I have a bad disc and sitting sideways with a tiller just wasn't working for me anymore...I wanted a wheel.
We looked at a 30' Cape Dory Intrepid for $10K, but this modern keeled interpretation of a Cape Dory had a Volvo engine and parts are getting nearly impossible to find for them. I read horror stories of owners missing whole seasons waiting for parts. Plus my Wife was uneasy about climbing up on the benches to get around the wheel under way. That meant a t-shaped cockpit. Well shopping for a $10K boat with a t-shaped cockpit netted very few candidates. Catalina 30's didn't get one until the mid 80's. That pretty much left O'days, older Cherubini Hunters and a few less prevalent brands. I checked out an O'day 28 after becoming convinced that was the boat for me. It just wasn't enough of an upgrade after the L25. What looked fantastic online really wasn't enough headroom. Plus the gelcoat on O'days tends to be really laid on thick and thus it had spider cracks everywhere.
I then found a Newport 30 owned by a guy one town over who was getting out of sailing. It needed to be converted to a wheel, but foolishly I felt I could do this upgrade myself. We got halfway through the survey before it was abandoned as the boat had hopelessly saturated deck core. We looked at a couple of newer Newport 30's but they had a new design with a fin keel. The hull lacked structural support aft of the keel and there was a huge dent in the hull of one behind the keel, possible from the keel being unable to support the weight of the boat. The other boat was absolutely mint inside but had cracks aft of the keel. My surveyor strongly recommended I abandon the Newport 30 and I agreed.
Somewhat dejected I refocused on Hunter 30's. During my first sailing experience on my Girlfriend's Father's Chrysler 26, their dockmates had a Hunter 27, which had seemed like a nice boat. To my chagrin, most that I found in my price range hadn't seemed to age well. So while looking for a good one I opened up my search to other options. That led to my finding an S2 9.2A nearby in my price range. I had actually been on a new one in about 1985 at a boat show and recall taking a brochure for this potential dream boat. Way back then I had focused on the Hunter 28.5...like I said earlier Hunter was attractive because of our neighbors H27. However, we had taken a weeks sailing lessons on a 28.5 up in Nova Scotia and what seemed a novel and attractive cabin layout to a 20 year old was less attractive to a 40 year old...climb over the settee to get into the vee berth? No thanks!
Anyway, I have hijacked this trailer post so I will wrap it up. So we saw the 9.2A and really liked the design. Nice glass work (S2 is known for it), nice cockpit, wheel, uncluttered interior and lots of headroom. However the blue tarp was tattered and scattering little blue snowflakes in the breeze. The nearly new ports had been improperly installed and had fallen off onto the deck leaving the boat largely open to the elements. It had clearly been on the hard for three or more years. On the plus side, I felt I could get a really good deal on it. On the minus side it only had a 1 cylinder Yanmar and needed a lot of work. My Wife stepped in again. She said "can't we spend more on a boat...if you buy this one I will never see you again because it needs so much work!" This led to the boat loan which led to Triple Play, which was the best 9.2A on the market at the time. It wasn't project free, but there is no such sailboat in my experience.