Hobie 16 / 18 vs Nacra 5.2
Depends on what you're into... if you want to race against others with boats like yours, find out what boats are around you. 99% going to be the Hobies, and more likely to be the 16 over the 18. If this is a boat just for fun or you don't mind racing on a handicap system, go for the best deal. All three boats you named have devoted followings, some more nostalgic than others.
Let us know what you get and how it goes! Good hunting!
I agree with John:
I have a Hobie 18 magnum and it's a terrific boat to be sailing because it's stable and I can easily single handle it. But, they're not making the H-18 anymore because of the transition to the Hobie Tiger, which seems to be for experts only if you intend to take advantage of all the adjustments and the spinnaker.
Racing the H-16 is a sure way to really get a lot of experience fast because you'll be able to race one-design and really find out what works and what doesn't. The Nacra 5.2 is a great boat if you don't intend to race. Kind of hard to get back on the trailer single handed, though.
Wyatt
Greg,
I have owned all 3 boats that you are considering, H16, TheMightyHobie18 and currently the N5.2. There are many considerations when choosing the right boat for you, such as where you are sailing (water depth). If you are going to be in a shallow area, go for the H16 due to no dagger boards. I would also shop around for a very good condition boat. Its worth the extra money to buy a nice used boat for $2K rather than buying a "fixer upper" for half that price. You will spend more time fiddleing around with problems when you could be on the water. I think you will find most sailors started out on a H16. The TheMightyHobie18 is a good boat, but very heavy and I found difficult to move around by myself. A couple years ago I bought a N5.2 from Jake Kohl and its way awesome! I would highly recommend this boat over the H16 if you have decent water to sail in so that you dont have to worry about hitting the dagger boards on a sandbar. I consistantly sail this boat solo, and have no problem moving it around. Replacement parts are plentiful too. Ive also added an I-17 spinnaker set up for the thrills.... but thats a different story!
I also know all three boats and would in a heartbeat go for a nice Nacra 5.2 in a heartbeat.That is, if you don't want to racein a Hobie fleet.
Great to single-hand and less chance to pitchpole that a H16 (I think this is my hang-up of which I'm deadly afraid, having gotten "killed" a few times in pitchpoling H16s and H18s).
Maintenance is also less on a Nacra 16, especially the simple rudder system. I think it's just more stable--also less chance of breakage. Older H16s have broken at the stanchions (or is it spelled "stantions"?).
Actually, I did not phrase this right: the H16 and H14 are more prone to pitchpoling, the TheMightyHobie18 much less so, although we did on a couple of occasions pitchpole the H18sx on really windy days, with 2 people on the wire and the skipper on the wing. Gusty winds of up to 35mph--and the skipper's momentary inattention did the trick. It is NO FUN to fly into the rigging of a H18sx!!
The Nacra 5.2 has slightly longer and straighter hulls than the H16.
The resistance to pitchpoling also has to do with rounded foredecks. They can go under the water at a slight angle and still pop back up. On a boat with a flat foredeck, it acts like a plow once it submerges causing the front of the boat to decelerate (while the back stays at the same speed!) and pitch downward even more. That's not to say that you can't pitchpole a boat like the 5.2 but it is a little more forgiving.
I've always managed to stay out of pitchpoling, but many times I had the leeward hull sinking up to the front crossbar. From what Jake says, I understand that on Hobbies the point of no return would come before. But the possibility to get the frontdeck underwater might be less on the hobbie than on the Nacra? The shape of the hulls give that impression
Gavin Colby: “The Hobie 16 doesn’t forward capsize [aka pitchpole] any more than a Formula 18.” Gavin Colby Interview Y&Y
Don't misinterpret my intentions because I truely believe that the Hobie 16 is a terrific boat for beginners to serious racers. I also think it may be better suited to someone entering the sport than the Nacra 5.2 because there's a much broader support base...Pitchpolling really shouldn't be that big of a consideration. Then again, I did start sailing on a Nacra 5.2. 
Although I'll admit to not having sailed a Hobie 16 since I've been experienced enough to make a comparison I CAN tell you that the Tiger F18, which has a flatter foredeck, is a lot less forgiving with the bow submerged than the Nacra F18 with it's more rounded foredeck. Galvin certainly has more qualification than me though
...but he does sail a Tiger.
We have done the following submarine act on multiple occasions on the Nacra ... and survived, pointy side up, quite easily as we did just after this photo was taken. Will a H16 come back from this?
P.S...I'm under that white water somewhere.
I’ve survived having the forward beam underwater in my 16 more times than I would care to admit. The fact is you need to watch out for the pitchpole thing with all catamarans. Why? Because they go that fast and they generally do not create dynamic lift. If you’re afraid of a pitchpole get a keel boat. Then again why not stick a mast in the sidewalk.
I am about to buy a Nacra 5.2 and I am glad to hear all you have to say about it. I singlehand alot and this was a concern as to if my 150# rump could soloright a Nacra. I have sailed on a Hobie16 quite a bit this last year while trying to decide which boat to buy. I really didn't want the H16 because with two adults (<350) it would really want to pitchpole bad. We would usually end up literally sitting on each other at the back beam and dump air. I have heard that the Nacras aren't so prone. In defense of H16s, these boats weren't exactly tuned to their potential.
I have a 5 year old son that loves to go out with me. How well do these boats handle kids? He is pretty helpful. He trims the jib and can probably work the boards for me. I've never sailed a cat with boards before. I'm looking forward to doing a normal tack. I learned to sail on monohulls and I always hated how slow cats tacked. Again, this was probably due to tuning, but we basically had to tack with the sails, the H16 would go into irons if we just tried to pull through like a centerboard boat.
I think you'll find that the N5.2 is a great boat for you and your son! It won't be any more difficult than the H16 for both of you to sail, and should be a lot easier to change tacks. Of course it helps to have a good set of main sheet blocks to allow the line to run free during the maneauvers. Check out the main sheet systems for sail on this web site (Catamaran Sailor) in the on line store. I'm using the 8 to 1 carbo blocks with 5/16" diameter main sheet. Makes for very smooth tacks! For more accurate tips, ask the master himself, Rick White....
New to the sport: Hobie 16
Have sailed a few years and have lots of friends that want to ride: Hobie 18mag
Want a fast single-handed boat: Nacra 5.2
Want to class race: Hobie 16
***Want to cruise: Hobie 18mag
I have had all three of these boats. The Hobie 18mag is a war-horse. Load it up and head out into the big wind and you will have an excellent time! The Hobie 16 is a simple, old boat. If you like to race and keep things simple, Hobie 16 is the way to go. The Nacra 5.2 is like a knife. Same level of complexity as a TheMightyHobie18, just 100lb lighter. Excellent boat for single-handing. Aftermarket sails can really improve performace. Just not that much deck space for two people.
Pitchpoling.... The H16 is easily the king of pitching. You have to be careful on any boat though. I haven't pitch poled hard enough to dump the TheMightyHobie18 or N5.2. I don't think it is important enough to worry about in the your buying process.
Jake, you are going to scare new sailors away talking like that. It's not like pitchpoling is inevitable, or is necessary in order to have fun. I've been racing on cats for 43 years and have never been involved in a pitchpole. We managed to have a lot of fun and win a few races along the way (maybe because we didn't pitchpole).
Rick has pitchpoled a couple times, but he never has when I am crewing, because I just plain don't let it happen. Of course, maybe that's why most guys don't race with women crews any more -- we just can't grasp the concept of "fun" and "pitchpole" being in the same sentence.
Yeah...well...I actually enjoyed seeing how deep (and for how long) we could drive the bows deep while reaching on the 5.2 knowing that capsize was inevitable. A small boat wake or puff would disrupt the sensitive balance we created and BOOOYOW! 🙂 The beauty of it all is if you are moving fast enough you get thrown clear! 
All that aside, we do not tempt fate so closely while racing and I can only remember pitchpolling once during an actual race.
as long as I raise the leeward dagger board up 3/4 or more so the boat doesnt trip over itself, I havent pitched it yet... and Ive had this boat on an absolutely smokin reach! I keep the jib soft and pump the main for all its worth while trapped out at the back of the boat! YOWZZAHH!!! Got to love that famous NACRA bow splash you get when its about 1 inch under water and drivin hard in the GROOVE!!!
If anyone pushes the boat so hard that the foredeck goes under, they deserve to pitch! 
In terms of pitchpoling (my personal PET PEEVE!), me and my long-time skipper NEVER pitched ourselves, only when it was another skipper! I mean, whatcha gonna do when it's blowing 30, your skipper CLEATS in the main, you and another crew are out on the wire, and your skipper falls off the wing??? You have only a second to try to get off the wing and try to uncleat the mainsheet. Actually, you have no time, because our H18sx pitched so hard that we came out black & blue from falling into the rigging.
The 2 of us are older now (total crew weight ca. 290-300), so we don't push it at all anymore and still have fun sailing our 4 boats (H16, H18sx, Nacra 5.8na). We like them all because they are so different.
I still say go with the Nacra 5.2.
It took me 9 years of sailing the Nacra 5.2 to finally pitchpole it. It happened very quickly but was not nearly as violent as when I pitchpoled my Prindle 16. I was not sailing with the bow submerged. I just hit a piece of chop wrong at high speed.
The boat did a cartwheel. Nothing Broke.
I righted the boat in less than 1 minute.
Most Important - check where your crew is before unhooking from the trap line in the water. The D-ring goes flying. I remembered, but I think that is the most dangerous part.
The pitchpole is not as violent as spinning out and catching the rail on a windsurfer.
We love the 5.2 - especially my Wife. It was the first sailboat she ever sailed.
See...you probably slowed down before you pitchpoled...if you were going faster you would have been thrown clear! (that's my theory anyway). I had dilegently checked the bow clearance before requesting the crew join me on the wire after round A mark for C in Charleston, SC. As soon as he popped out, we received a monster gust and pitchpoled my 6.0 so hard that the boat shot straight down and popped up backwards like a cork. As the boat was driving into the water and came to a screaching hault, my crew and I were skipping across the water out in front of the boat. The boat launched well clear of the water and landed about 12 feet downwind of where we pitchpoled. I do remember thinking how strange it was that I had to swim 10 feet downwind to get to the tip of the mast. Later that evening, the guy driving the RC boat poured me a beer and told me what happened and that it was the most spectacular thing he had ever seen! We were not being terribly serious during this race but the the gust really did catch us by surprise.
Disclamer: Don't try this at home.
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Let me know if you ever need the steps to raise and lower your 5.2 mast single handed... It's fairly easy and safe. I have to do it quite often to sail by myself too...