Reddit mentions of Seaworthy Offshore Sailboat: A Guide to Essential Features, Handling, and Gear

I find there's a lot of information on forums for popular boats regarding their mechanical and construction deficiencies. E.g. Discussion on certain boats getting blisters, or needing bulkhead replacements. However, there's basically no information on design deficiencies, and most of the discussion you do find is pure speculation. The reason for this is because boat design is more of a tradeoff of different qualities. You want to research these qualities as much as possible. For instance: displacement, sail area, keel type, hull construction, cabin layout, cockpit size and layout, water line length, ability for the boat to right itself and how it affects stability, etc. Most of the information on these subjects is available on books and not necessarily easily accessible on the web. Here are some good books:

• http://www.amazon.com/Inspecting-Sailboat-International-Marine-Library/dp/0071445455
  
• http://www.amazon.com/Twenty-Small-Sailboats-Take-Anywhere/dp/0939837323
  
• http://www.amazon.com/Seaworthy-Offshore-Sailboat-Essential-Features/dp/007137616X/ref=pd_sim_b_1
  
  Now, these books are slanted on offshore sailing which is what I'm interested in. You didn't specify where you'd be sailing or how you'd be using it. My guess is general weekend cruising.
  
  So no, I haven't seen any discussion on the differences between boats like that. You have to make an informed decision on the data available (e.g. of sailboatdata.com, class association sites, owner postings on forums, etc). Best thing to do is ask people who have knowledge once you've narrowed it down. The truth of the matter is, no matter what boat you get you will have to deal with the tradeoffs. Some guy saying that "X" boat is slow or fast is completely subjective and doesn't mean a damn thing to you. You have to figure out what the qualities you want are first and find the boat that best fits those qualities.
  
  Lastly, if this is your first boat please go small and with something that you can easily sell again. Chances are your wants and needs will change, and dumping a whole bunch of money into the wrong boat may be a big mistake. Get something simple that is easy to maintain, so you can learn how to properly maintain a sailboat. The mistakes you will make will not be a big deal on a small boat, but if you buy a 40 ft Catalina a small mistake can balloon very quickly.

I wasn't thinking of wind exposure on the large windows, more like what can happen when a really big wave hits them :)

It really comes down to personal comfort. For myself after I do some island hopping I've been looking at maybe getting a Tayana 37 cutter for ocean hopping. Small windows, full keel, small cockpit, plenty of sail and fuel, a proven world cruiser.

You might consider buying this book: http://www.amazon.com/Seaworthy-Offshore-Sailboat-Essential-Features/dp/007137616X/ref=sr_1_1?ie=UTF8&qid=1342194688&sr=8-1&keywords=offshore+boat

Basically learn up on the sort of features you need and then make a call on whether or not your boat can be modded to get it to the point where you'd be comfortable make the trip.

But at at certain point, to me, it becomes better to buy a different boat. For example I have a Pearson 323 now and I could mod her for an Atlantic trip. Re-inforce the rigging, maybe add another compression post in the cabin to add structure, toss on a liferaft and rig her up for a drogue.

But considering she's worth 20k and for 50k I can get a nice Tayana 37 it doesn't make much sense to toss 20k into her to rig her up for a trans Atlantic trip. Especially when you consider that any buyer looking for an offshore boat isn't going to be shopping for a heavily modded coastal cruiser. I'd basically be tossing "offshore boat" money into a "coastal cruiser" market. I'm better off buying that Tayana and putting offshore money into her.

But maybe you don't need to add much to your boat for a 1 off Atlantic trip. In that case it may make sense to get to the bare minimum of your comfort level, wait for the best time of year and then head on out, enjoy yourself and come back home.

I'd just really research up, learn the risks and just talk with your significant other what level of risk you're comfortable with. That's really the important part and everyone is different in that regard.

This one?