Occasionally people ask my opinion about "features" to consider for a cruising sailboat. Some features are a matter of personal tastes, affect comfort, enhance performance, or increase safety. All features come with a cost, and more often than not there is always a trade-off.
Now, with that being said, I tend to approach the question differently. I do not start by offering a laundry list of features I think are good, or "must have" on a sailboat. There are certainly features I desire, but I always start by discussing things that would eliminate particular sailboats from my consideration.
So, without further adieu...
Wooden or ferro-cement hulls.
Unless you are a glutton for punishment, enjoy splinters under your fingernails, raise Toredo worms as a hobby, and like the musty smell of water soaked wood then I highly suggest staying away from wooden hulled boats. Yes, wooden hulled boats are fine works of art, and beautiful to gaze upon. All boats depreciate in value, but wooden hulled boats not only depreciate in value, but it clearly costs more to maintain a hull that is in a perpetual state of deterioration. Owners of wooden boats will of course deny these problems. But, a walk through boat yards will reveal the truth.
Ferro-cement hulls are not just a bad idea, they are a stupid waste of money. Most ferro-boats are "back-yard" built using cheap materials (i.e. steel rebar and chicken wire). The homemade layups are often clunky looking affairs. The steel used to 'reinforce' the cement will eventually rust thus weakening overall hull integrity. Hull repairs are difficult to impossible. Connections (i.e., chainplates, etc) are weak because ferro-cement requires distributed loading for structural integrity. If you look for ferro-cement boats for sale on the internet there are many reasons why they can be had for a song and dance...so just say no!
Finally, before you plop down money on that sweet deal for a wooden or ferro-cement hulled boat...you had better check on your ability to obtain marine insurance for the boat.
Spongy Decks & Hull Blisters
It is not only wooden and ferro-cement hulls that have maintenance issues and potential problems. Poorly bedded deck hardware on a balsa cored fiberglass deck can lead to rot and a spongy deck. By the time the deck feels "spongy" the damage is pretty well advanced. And if it not properly repaired it only continues to get worse. Merely drilling a hole and injecting epoxy is not a proper repair. While all deck hardware should be rebedded periodically, tearing up the deck to replace rotted balsa is not periodic maintenance.
Another problem with some fiberglass boats mostly built in the 70's and 80's is hull blistering or "hull pox." There are several causes of hull blistering, including poor layup and wetting out of the fiberglass cloth, chopped fiber layup, poor quality resins, experimental resins, and oils or other foreign substances in the mold. (See this article.) Hull blistering can occur both above and below the waterline; although it is more commonly found below the waterline. Some people will claim that blistering can be fixed by grinding out the blistered areas and filling with an epoxy compound. Usually this is only a temporary fix. So, if you don't relish spending your time in boatyards grinding away at fiberglass every few years stay away from hulls that have the pox.
Teak decks (outside teak in general)
Traditional screwed down teak decks an are beautiful when they are well maintained. Teak also provides a good foot hold at sea even when wet. But, here's the reality. Someone took a perfectly sound fiberglass deck, drilled about 1001 holes in it, then laid down strips of teak and black caulking and screwed it down. Besides the whole affair required to maintain their good looks...when they leak (oh...and they will leak), tracking down the leak will require you to literally remove 293 screws, cut the sealant between the boards, and pry up 3/4's of your deck's teak strips . If a leak is detected in the aft starboard berth, I recommend you start pulling teak strips near the bow on the port side and work your way back. Eventually you will find the leak, and maybe a few more that were hidden but turning your deck into a fiberglass encased sponge. Oh...then you have the joy of re-bedding all that beautiful teak deck and pray to Neptune it doesn't leak.
External teak trim looks great when well varnished. I have stock in 3M and I really appreciate everyone who buys 3M products (blue tape, various grades of sandpaper, brass wool, etc.) and dedicate unending hours to perform brightwork on their boats. I sincerely thank you. As for me...I'll go with stainless grab rails, and aluminum toe rails any day of the week. On my current boat the only external teak is 2 dorade boxes, and the companion way frame and door...it is all beautifully maintained with 3 coats of white epoxy paint.
I love cutter rigged sailboats. I sometimes wish Discovery was rigged as a cutter. But, some sailboat manufacturers like to add a feature called a "self-tacking jib" using a jib booms, or club-footed jibs. Whatever else you want call them these toys are for lazy pond sailors who never venture beyond the boundaries of their cockpits onto the foredeck unless they are securely tied to a dock (and only then to brag to the neighboring vessel how easy the jib is to manage). I do understand they can make tacking easier and provide better sail shape. But, having worked the foredeck on my share of boats I'll tell you now that there is no way in hell I would leave the dock with a piece of aluminum or wood that swings across the foredeck. There is a damn good reason this apparatus is also referred to as a"widow-maker." I personally would not want to be swept over-board after having one or both legs broken as the deck-sweeper apparatus slams across during an inadvertent jibe. I also like having an uncluttered foredeck both underway and while at anchor. Your preferences may be different.
Long-Armed Anchor Rollers
Anchor rollers that barely extend beyond the bow do not accommodate modern anchor designs very well, especially the Rochna, Mantus, or Delta anchors. So, some manufacturers are extending the anchor roller well beyond the front of the plumb-stem bow. And Lewmar, WhiteCap, and Windline also make extended anchor rollers for people who don't want their anchors to bang against the boat's gelcoat. Who can blame them? But, I recall a story by Lin and Larry Pardey about a sudden squall that hit a line of sailboats in Mexico that were anchored stern to shore. The majority of boats ended up on the beach in the aftermath of the storm. In a survey of the beached boats every a long arm anchor roller had been bent and twisted from the violent up and down jerking of the 8 - 12 foot waves generated by the storm. I am also personally familiar with a situation in which an after-market long-armed anchor roller was added to a boat. But, while docking the owner misjudged the distance while turning into his slip catching the anchor on a concrete piling while docking the boat. Needless to say the anchor roller didn't survive, and there was pretty extensive damage to the stem and foredeck as well. Lesson learned....put a piece of stainless steel plating on the bow to protect my bow from the blade of the anchor.
Main Sheet Travelers in the Cockpit
I had a San Juan 23 that I sailed extensively throughout Southeast Asia for about 3 years, mostly around the Ryukyu archipelago. The shoal keel with a swing fin made this boat ideal for those uncharted coral heads that I inadvertently discovered frequently; however, it was very cramped inside. If you are not familiar with the San Juan 23 it also has a traveler that sits in the forward part of the cockpit just in front of the companionway. Let's just say this setup is less than ideal for those people who value their heads, do not want to be strangled when poking your head out the companionway, or don't want to negotiate a rope obstacle course between the cockpit and the cabin.
Same applies for travelers elsewhere in the cockpit on a cruising sailboat. When designing something to add, or rejiggering an existing "feature," I always try to envision the worse thing imaginable that can happen on a boat, and then I try to figure out a way to prevent that worse case scenario from happening, or do something to minimize damage or harm. Think of that fancy racer-cruiser with that nifty traveler running across the cockpit - because that's how racer's have it rigged and it looks really cool. Now, imagine your wife or girlfriend stepping over the traveler to hand you a drink and stand beside you in her bikini looking sexy while you're standing proud with one hand on the helm and another around her waist. Both of you smiling. That's a really nice picture right? Now imagine a rogue wave hitting you from behind, or a wind shift as she is straddling the traveler and the line is not secure, or gives way. Then imagine the traveler car and main sheet slam to the opposite side of the cockpit where she was trying to cross. Now realize that you don't have that drink in hand, you don't have a sexy woman in a bikini next to you...and tomorrow you're single-handing your boat.
Dual Helms in the Cockpit
Perhaps the most ridiculous feature modern boat designers are putting on cruising sailboats...opps...sorry I mean racer/cruisers is dual helms in the cockpit. Let me state that some sailboats are well designed for racing, and some are well designed for cruising. The so-called racer/cruiser is a unicorn...it does ok as a race boat...it does ok as a cruiser. Sure...the dual helm looks really cool...I bet the guy who got the tattoo of a spider on his face (seriously...Google it) thought it looked pretty cool also. The dual helm is highly functional on high end race boats because it provides the helms person great visibility. On a cruiser it only occupies valuable cockpit space. Also...when you are cruising...coastal or blue water....you spend very little time at the helm because the boat is on autopilot or using wind vane steering. But, one the bright side while your are cruising and the boat is self-steered, or while resting on the hook in a tropical anchorage you do get the pleasure of sitting in the cockpit and looking back at the dual helms and saying to yourself..."geez...those two helms look really cool."
An athwartships berth is a bed on the boat in which your body lays from side to aide at a right angle to the keel. These berths may be comfortable at dock or one a lake without a single ripple. But, in an anchorage with any sort of surface motion imagine yourself laying in a bed as the boat rocks from left to right...sometimes gently...sometimes violently. If there was anything designed to induce vomiting it is an athwartships berth. To induce further nausea some sailboats cram these athwartships berths under the cockpit. So, not only are you laying longitudinally in a boat that rolls at anchor, you're crammed in a space with little ventilation, and a fiberglass ceiling 6 inches in front of your nose. But, if you are not at all claustrophobic and completely immune to seasickness an athwartships berth does allow for more room in the main cabin.
Now, I know there are many people who will contradict or suggest I am overstating certain concerns. That is fine; we all have our own experiences and perspectives. I am providing my opinion based on my experience, my observations, and my personal likes and dislikes. My biggest like is sailing comfortably aboard my boat. My biggest dislike is being uncomfortable while sailing or spending weekes working on my boat on the hard.