Here' s my 2 cents and that's all it's worth. Maybe 3 cents, it got really long.
I have sailed but not owned 14s (recently) and 16s (about 10 years ago) and currently own an 18(magnum). I am 49 years old, 6'2," and weigh anywhere between 195 and 230 (currently 205).
14:
The 14 is a sunfish on steroids. one person can toss it around on the beach, sail it, rig it, and right it easily. That is really the way it should be sailed. It can carry 3 adults (barely) but will not point or tack with any more aboard. If you can get the jib/turbo rig it would be really worth it. They haven't made it for years so don't look for fleets to race with. Also parts while available can be hit and miss.
16:
16's are ubiquitous. I've seen them car-topped. If you want to class race this is the boat for you. It's really a two man boat but one person can rig,sail, and right it, and drag it around fairly easily. You can get a spin as well as other upgrades so unless you're slumming from 12 meters it can be as challenging as you want to make it. The tramp sits up on pylons so you stay a lot dryer. It's also still in production which is nice. The 16 is kind of the sweet spot of the Hobie line. I wouldn't sail it with more than 4 adults.
18:
The 18 is an enigma. It can be had in a myriad of shapes and configurations.
The bad:
They are all an order of magnitude more difficult to deal with on so many levels. A lot of states start to register/title boats at +16 ft. I'm a big guy and dragging a 400+ pound boat around by myself is trying at best. Stepping a 30 ft mast is "interesting". The daggers are a real issue in shallow water. Diamond tension, spreader rake, mast rake, pre-bend, etc all add to the challenge. Righting is MUCH more difficult and I'd recommend some mechanical help, even with 2. If you want to solo it you had better be on your game. It's f18 legal but probably too heavy/old to be really competitive. In short the 18 is a big, FAST, technical boat. It's also been out of production for years and you'll probably own the only one in 5 counties.
The good:
Having said that, with the magnum wings on it''s almost a party boat. (SXs are bigger). I've had 5 adults, a big dog and a huge cooler out with plenty of room and had no problems pointing or tacking in light or heavy weather(could maybe have brought 1 more). The daggers really help upwind and tacking. I'm still learning and even without tweaking all that stuff I knock around the bay, through the sound and up the river with the family friends and dog without worrying about getting the last ounce of performance out of my rig. It has all those tweaks that "real" sailboats have. As I learn all that stuff the boat will grow with me and I will become a better sailer as I work towards my run at the America's Cup (or more likely a retirement cruising the carribean). AND I can add taller masts, square head sales, battened jibs, and spins as well as bigger downhauls and main blocks. In short the 18 is a big, FAST, technical boat. AND it's f18 legal if I (or my son) want to race it so having the only one in 5 counties isn't that important if I don't mind losing. I've only soloed it a little but it's a rush and once I acquire a hiking stick and a righting bag I intend to push my limits. It is MUCH bigger, more stable, and seaworthy than the 16. Someone once sailed an 18 ACROSS THE ATLANTIC!!! I feel much more confident sailing it out through the passes and the surf into the gulf and to the outer keys. I am planning some overnight cruising/camping trips with my son that wouldn't be possible on a 16.
Summary:
I'm enjoying my 18. With my(wife's) goal of a cruising retirement, my enjoyment of a technical/physical challenge, and enjoying sailing with friends/family it's a good choice for our family. Under pretty much any other circumstance I'd have bought a 16.
John
_________________ The ox is slow but the earth is patient
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