Trying to decide between H16, 18 and 21SC

Hi all,

My background:
I’m moving to Cleveland in a few weeks to start a new job and have always wanted to get into the Hobie sailing scene. I’m 6’0” and weigh ~145 lbs. I’m looking to buy a Hobie Cat and start sailing on my own, but I’m not sure which Cat to get. I’ve been sailing once on a Hobie 16 I think (no jib) a few times on some small monohulls and crewed for a summer on a 36 foot J boat (I believe) participating in casual weekly races. I’ve obsessed over Hobies for about 6 years now and have read as much as I possibly could about rigging and sailing and even racing them. I’ve been boating with my family on our 19’ and 27’ Grady’s as far back as I can remember, and I’m very confident that I know how to handle a small sailboat competently. Tuning the boats and the finer points are still a bit fuzzy, but I know how to get from point A to point B and I have a good idea of how these boats work, and I’m eager to learn.

What I’m looking for:
I’m looking for a versatile boat. I want something fast, that I can fly a hull and go out on the wire on, maybe even do some racing (it looks like a very fun and exciting aspect of sailing cats). I expect that I may end up sailing solo 35% of the time, sailing with a crew member 55% of the time and taking out a few friends the remaining 10%. I would like the versatility to be able to bring at least 3 friends out with me from time to time. Finally, I’m hoping to be able to get a boat in decent shape for under $2,000 if possible. I realize that these are conflicting goals and that compromises will have to be made.

My options:
I have always really, really liked the 16 for the simplicity, raised tramp and speed, and I’m sure that the trapeze on that boat is like none other. I also like the option of adding a spinnaker (waay down the road). However, I’ve heard that it’s a very easy boat to pitchpole. I like the 18 because of the extra space and (I’m assuming) higher weight capacity… or at least the higher freeboard. The wings are a really neat idea as well, the roller furling jib seems to make soloing simple enough and dagger boards don’t really scare me. There is also a 21 sport cruiser for sale in my area, which I’d really like to get my hands on just because of the large capacity, storage space and forward tramp (and it looks like a blast!), though it’s a little pricy and I reckon it would be impossible to get parts for. I also don’t like how high up the boom is, seems like you’d lose some efficiency that way. I feel like the 16’ll go fast with 1 or 2 people, but the 21 can go for long cruises or 'adventuring' without getting cramped.

I may be a little overly optimistic as to what I can handle, but rest assured that I am very enthusiastic and very dedicated to learning the ropes.

Well....You're right about having to make some compromises. There is NO such thing as the "perfect boat".
6", 145lbs. - definitely the Hobie 16. Large racing fleet. Sailing solo or with a crew. Take several friends out sailing if they're not too heavy. Otherwise, take them out one at a time. No daggerboards is really a nice feature (assymetrical hulls). Fast. Versatile. Easy to get parts. Under $2000???? Yeah, but spend a little more and get a boat & trailer that's ready to sail now, and not repair first.
The raised tramp will keep you sailing drier. You can take it on long cruises. The tramp is very comfortable to sleep on when camping, or sail with a crew who can share the skippering responsibilities and the crew can take a comfortable nap when the wind is light. Trapping out when the wind is stronger is a blast! You can add a spinnaker in the future if you wish.
Pitchpole??? It's not a pitchpolling machine. You have to really screw up in order to pitchpole. It seldom happens and when it does it's your fault; not the boat's fault.
There are other good choices, but I believe you'll be happier with the H16.
When you get to Cleveland find a nearby Hobie Fleet. They'll be able to help you rig, sail, and find races.
Good luck!
Richard