You are all over the map.
You are right - I am.
I consider myself on the lip of a large funnel. I don't know how long it will take the lake house to sell but I expect this buying process to take about a year or so. My heart says either a Ford F-250 4x4 pickup with large wheels (Island Packet, Pacific Seacraft, etc) or Porsche Boxster (J80). My head is saying Honda Minivan (Beneteau, Jenneau, Catalina, etc) and my wife is saying go get the boat of your dreams. I guess I posed the question to determine if there is a Porsche Macan of sailboats that would offer me close to j boat performance with comfortable accommodations and a salty appearance for my proposed budget. I couldn't really seem to find anything and wanted to see if others knew of something I'm missing. My reason for posting now was to try to maximize the two days I'll be spending in Annapolis.
I'll probably be keeping to boat in Charleston or nearby. What I have learned from my past ownership experience is that: I don't like to trailer, that I used to judge a boat from the interior pictures - now I fully understand I'll be spending 90+% of my time in the cockpit and that for my purposes deck layout is important, shallow draft is nice but not essential, I loved my CD25 but dealing with a full keel at the dock with a ripping tide was not fun, my CD25 took a good bit of wind to move her, my H212 was way too tender for the family, and while my C30 was a great boat at the time it was just not as satisfying to sail as the j24 or j80, I don't have the time or aptitude for a project and I like newerish as opposed to olderish. So I think what I am looking for is something that has the accommodations of a Beneteau, the performance and underbody of a J Boat and the exterior of a Tartan all for a reasonable price! Sigh.
If I owned a house or condo at the coast I would buy a used j80 and be done with it - or maybe a nice j100 or AE28 if I was feeling rich. The need to stay overnight on occasion complicates things a bit from my perspective. A house at the coast isn't in the cards for another 10 years or so. I need something that should carry me until then and hopefully will continue to satisfy me for many years beyond that.
I threw the Marshall out there because: I think they are pretty, they seem to be ruggedly built, I think it would be easy to daysail with the family, while I've never been on one I did sit in a Sandpiper cockpit once and thought it was super comfortable, the centerboard means I could explore rivers and creeks and there is something to be said from a practical standpoint of owning a boat that is just 22 feet in length. Plus, they don't seem terribly expensive. I'm not sure lacking standing headroom would make me happy if I do cruise her and the thought of gybing in a blow does make me a bit weak in the knees.
For what I need a C30 or 30ish Beneteau would work fine. I was hoping to get feedback on other designs that would offer either more performance and/or a saltier appearance that would still fit my proposed budget and need to single hand from time to time.
My wife is being super supportive but I think I get one shot at this!
I hope this explains some of my schizophrenia!
I do appreciate all that folks have already contributed.