Hi Eric. According to an above post, your intro set a
record. So I thought I might as well go on and see if I can set another. This is my first post on this forum, and I guess I might just step into the Besserwisser role I'm comfy with. :-D Actually I read your post to get a feel for what level of presentation I should make. I guess I ran into the highest hurdle first. Still, as I'm far from new to sailing, I think I may be able to say something you may find useful. And then I'll go on to making my own presentation thread (but less wordy than what I write now)...
First. Congratulations on discovering a beautiful hobby, or way of life, or addictive drug, depending on how far it has evolved in you. Most likely you will end up in the last of the categories sooner than you'd expect. I got to that 11 years old (38 years ago), and I still love it endlessly.
I will not try to answer all of your questions, and the ones I address, I'll mostly not answer fully. Many of them are rather big topics, and deserve their own threads to give you the info you search. What I will try to do, is illuminate the essential questions you need to answer, and point a few fingers in possibly useful directions.
OK. The first big thing here is
what do you want from sailing? You partly answer this yourself, but this is a typical trick question. True answers quite often become wrong very quickly as your familiarity with them grows. My impression is that you enjoyed the Hobie Cats for the playful fun of it and for making you laugh out loud. The other things you do, indicate that this is generally an important aspect of why you choose the things you do. You're probably a rather energetic fun seeking guy. This forum is dedicated to cruising, which is an absolutely wonderful thing, but is is a totally different thing than the play that woke up your fascination for sailing. I strongly identify with the side that showed you "the force". :-) I also have crossed the Atlantic and cruised the weirdest of places and love that too.
I think you should consider if you maybe should do one step at a time. By that I don't mean that cruising is on a higher level than dinghies, but that you should follow the obsession you already have and let other related ones grow on you. And cruising is one that will do so. This sequential way of approaching sailing will have several benefits. The most important one is that you really learn the art of handling sailing vessels the exact right way. Small craft that can toss you into the drink, have an extremely much better ability to teach your backbone how to do the thing intuitively. Bigger boats will learn you other stuff better, but that real hands-on physical KNOWING why the boat behaves as it does, can ONLY be learned on dinghies. (Small cats are of course dinghies as well). In a
dinghy you learn in one day what a slightly bigger boat teaches you in a year. I'm also a fairly accomplished
racer, and I've done that as a profession: I claim there has never been a profoundly good sailor/racer that has not extensively sailed dinghies. Some get offended, but that doesn't change my view on this.
Learning the art of sailing as I recommend, is probably very close to how you got good at white water stuff.
So the
Nor'ship 27. I have never sailed one, but have sailed resembling ones. It looks quite much like the traditional small wooden boats from the North Sea (south west) coast of
Norway. Now though, they have mostly been motorised. Maybe the
designer found inspiration there, and the name indicates some too...? Anyway, it should be a very reliable and, for its small size, fairly comfy cruiser. Looks nice too. It will be capable of crossing proper oceans and handling real bad
weather safely, but it will take time and be rather wet and bouncy.
Maintenance costs for a reasonably well kept one should be quite
cheap. It's a sailboat, so the engine should preferably not have too many hours on it...? Keeping real big boats, or doing serious racing, will cost you a LOT. A small cruiser like this is very manageable. The trailerable feature is in my opinion a very good thing. It lets you go to different places to explore them without the struggle of going there very slowly before you can spend your hard earned spare time pleasurably. And the big BUT is: This boat is probably a real winner in what it does, but sailing this boat will give you absolutely zero playfulness. Given what I said above, you get my drift.
I think my main points have been presented. I'll just jump through a couple more:
Build your own boat? I have designed and built racing boats, and I will also build long distance cruisers, but quite different from the normal. That's my reason for building. Can't be bought. Generally when people ask, my recommendation is this: If you want to build something, for the pleasure of building and creating, a boat is a good thing to build. If you want to have a boat, buy one! The hours you spend building will never reflect the actual savings, nor be worth the time
lost from your loved ones and other things you like. Also the finished boat will in 99% of the cases be an obvious home built boat that is not the beauty you imagined and is almost impossible to sell at a reasonable price. It really IS possibel to achieve the opposite of what I say here, but then you need to really know what you do. You need to be as good as a pro
builder or better.
Creature comforts. :-) Sailing is not comfortable. Sorry, but that's just it. Still the differences between types of sailing, places you sail, boats you sail and the style of sailing, is HUGE. The Nor'ship27
offshore in a blow is pretty close to the worst you can get, comfort wise. And sleeping inside in calm but hot climate with no AC can be rather bad , but not quite as unbearable as one might fear. Much of the
hull is immersed in the sea, which will rarely be above 27 degrees even in the Keys etc. The air inside the boat will be slightly cooled by this, but expect just a slight improvement. If it's slightly windy there is no problem. You can use
wind ducts etc to move the air inside. Also sleeping outside is very nice, provided you are somewhere without mosquitoes... :-D
I mostly sail fast multihulls of different types, but have sailed all kinds of other boats too. For sailing in relative comfort, there is no way around moving into cats. And the difference is astonishing. The comfort I speak about is not at all related to space (which the also have MUCH more of) or
equipment and luxury (which the tend to have too), but there are two very notable differences.
1 Monos and cats move very differently. Monos heel over (a lot) and the heel varies much. It's bow will slam into waves and the pitching movement will for most boats be quite much more than the actual waves the boat is crossing. Monos tend to act like pendulums. This is especially bad when there are waves but no wind to give a stabilising pressure on the rig. Cats have quicker more jerky movements, but just slightly. Their heel vary very little. They
pitch much less and tend to even out or contour the actual wave patterns.
2 A mono is heavy and a substantial part of it is under the water surface. Moving in a chop or heavy seas, it will cut through waves and particularly small boats will be in a constant heavy sea spray. Inside it is called "below decks", but may also be called "in the cellar". Light comes in through hatches in the
deck or small areas of glass well above your line of sight when seated. At best, you see the sky. Cats are a totally different beast at this. Even down in the hulls, you're higher up. More important: When you sail the boat and most of the other time you're on the boat, you spend on the bridge
deck. This may or may be covered but will either way be much drier than the
cockpit of a mono. If inside the bridgedeck
cabin, there will be a generous view in most directions and plenty of light and air.
The effect of these two profound differences, is that sailing a cat especially to windward, is very much less tiresome. Quite often I've sailed a short day between harbours, having a very nice
cruise, dinner with wine and all aboard, also totally non sailors, enjoying the beautiful day. Arriving in the harbour friends from the last harbour that left at dawn have just arrived and are totally fatigued by the "horribly strong wind and big waves". Truly two different worlds. I will never again go long distance cruising on a mono...
Well. Now I have said the essentials of what I thought while reading your post, I've declared my religion (multihulls :-) and I may have set several new records for first posts on this forum. I hope this is decently readable, as I haven't read through it, and as my native language isn't
English...
Welcome to the beautiful world of wind Eric, and good luck at finding your path towards unavoidable fanaticism. :-D
Stein