A trailerable boat appears to be a way to reduce operating costs, but if you think about it for a moment, what you are saving in marina fees is burned up in your hours spent launching and rigging the boat each time you want to use it. Here in Canada our sailing season is short and one counts every sailing day as precious. Mucking around with stepping the mast is impractical here.
The reason a trailer for one's boat is desirable is that the trailer can extend one's cruising range given a limited period of time. My friend's Contessa was towed from Ontario down to Florida for a three-week adventure in the Bahamas. Another friend of mine sailed his boat down the St. Lawrence River (with the current and the prevailing winds) and then used a trailer to bring the boat home again -- the trailer made it possible to travel further and concentrate on the enjoyable parts of his trip.
The Contessa appeals to many because it is perceived to be the cheapest proven boat for a trans-Atlantic. Very few people actually make the trip but they are drawn to the possibility. It is a bit like your truck. It appeals because it can go almost anywhere 4WD can go, but in practice, many Excursions never leave the pavement.
My suggestion then is that you you should visit your goals for your sailing this season. Because your budget restricts you, be objective and decide what boat do you really need.
By far the best way to lower the cost of ownership is to not own at all. There are LOTS of people looking for crew. Their boats are often in prime areas and, in time, a friend may allow you to 'borrow' their boat. If you have not yet sailed a Contessa, crewing is a superb way to learn the boat.
What kind of sailing do you want to do? Picnic sailing, blasting around in big winds, racing, coastal camping trips, trans-Atlantic? The Chesapeake is renowned as a sailing destination and you need go no further for years of adventure of all kinds.
Are you intending to sail alone or with a group? All the time or mostly alone?
Let's say your time is cheap and you are committed to owning a trailerable boat. As you've learned from these posts, the Contessa is not an optimal trailer-boat.
While not pretty, a Macgregor 26 is a practical trailerable boat -- and with a 50hp outboard it can cover a lot of distance quickly when the wind dies. I know a fellow who has a center-boarder Sirius 21 which he has towed and cruised all over Canada and the US.
You can go smaller too. There are books describing some great trips in small open boats such as Wayfarers and Lightnings. Sailing Raids have become trendy in the last few years -- basically open boat sailing from point-to-point with camping at each end. The smaller the boat the easier it is to launch, rig and maintain. And smaller boats cost less too!
Here is the best news of all: regardless of the boat, your choice is not permanent -- you can quickly sell the boat and get a different one which better suits your objectives.
You have many options and I do not doubt that the members here will be happy to weigh-in with great ideas. Contessa owners are a friendly and supportive group. Tell us what you need!
Cheers!
Christopher