Join Date: Feb 2000
Location: Annapolis, Md
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I would say that much in your question does show a bit of lack of the kind of basic knowledge that it would take to voyage offshore safely in a small. While I am not suggesting that a Cal 20 is a suitable small boat to go offshore on without major mod's, the particular points that you raise are worthy of comment.
Historically, outboard rudders were the preferred rudder for offshore use on small boats. Small boats cannot carry the spare parts to make a spare rudder or major repairs to an inboard. The comparative light weight and simplicity of an outboard rudder and their ability to be unshipped and repaired and rehung, made them the hands down favorite for offshore small boat sailors. That said, they need to be properly engineered, constructed and installed.
Similarly with the shroud attachment point. It does not matter whether the shrouds are attached through the deck or to the hull. In either case, it is important that there be proper reinforcment of the hull, and hull to deck connection in the area of attachment. Typically, this is by some combination of hanging knees, longitudinal stringers, bulkheads and flats. I would be surprised if the Cal's shrouds are only attached to the deck, (they wouldn't be the only small boat to do that) but more likely than not there is some addition reinforcing that make that possible. If not it would be moderately easy to add.
Now then, in the bigger picture, I really question that you will be able to find a true offshore ready boat for under $5k. Anything that you are likely to find in that price range is bound to be tired and in need of moderately expensive upgrades to go offshore. At the very least I would be skeptical that you will find a $5k boat with offshore capable sails and adequate tankage in that range.
If I had to look for a suitable boat as a platform for what you propose, I would try to find something like a folkboat derivative (Henry Walton had a really nice fiberglass folkboat built in Canada in the mid-1960's an example of which I have seen offered for sale for $2500 in the States), Sailmaster 23 or 26, or perhaps a Tartan 27, rather than the less suitable Carl Alberg designs that you often see touted on the internet. But whatever you find in that price range, you better be prepared to spend a lot more than $5000 to make the boat suitable for offshore use.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay