Advice on purchasing a blue water yacht - HR 39/40?

The HR 40 is a great choice but has a limited fuel tank and is quite dark and I think it will be shame to be in such dark surroundings, you might find it quit hot below decks. I would seriously look at something like a Wauquiez 48, I think you will find it just as easy to handle and much a much nicer place to be sitting, you can see out from inside and enjoy the view. They have bigger fuel tanks and the one below has a washing machine and carries 800l of water and 600l of fuel.

http://www.yachtworld.co.uk/boats/2002/Wauquiez-Pilot-Saloon-48-3053095/Portugal#.WLIXGBiOpdA

You could also get an Oyster 45, again almost a deck saloon so much lighter and plenty of fuel and water capacity ant tons of room for your stuff.

http://www.oysteryachts.com/brokerage/fleet/free-mind
 
Looking back at your requirements, if a centre cockpit is not a conditio sine qua non, you should take a serious look at the Starlight 39 Seven Spades is selling. Very good build quality and frankly a much better sailer than HR. Doubts about blue water capabilities? Have a look here:http://www.kindofblue.info, a Dutch couple completed their circumnavigation in a Starlight 39 without problems.
I must confess to a certain bias about Starlights ?
 
The average yacht size in the Caribbean is circa 44ft. Most are sailed by husband and wife. If you were sailing here in the caribbean with a 40 footer it would be considered on the small size. . Our 44ft boat is pretty full of gear. We can make space for visitors but it means a lot of rearranging of our kit. Liveaboards have quite different requirements to summer holiday cruisers. The kit tends to grow the more liveaboard cruising you do. The ability to buy supplies in bulk when the price is right is useful but needs good locker space. Large tankage is also very useful. There are anchorages here where we wouldnt want to make water. Sitting in an anchorage for several days on good quality tank water is nice. Being able to engine for several days due to a large fuel tank makes a difference.
A large cockpit for entertaining guests that is also protected as sea from the elements is a must for us. Tiny sprayhood that only stop spray from going down below are no good to me, i want protection from the weather and comfy cockpit cushions that are not covered in salt water due to flying spray. I also want a boat that sails exstremely well and can go well to windward. This means deep draft and a powerful rig that drives the boat in light winds as well as heavy weather. If the boat slams to windward or gripes up in a squall I have the wrong boat.
In hot weather we live in the cockpit because its a great place to be not be ause its too hot below. Excellent ventilation is a must. Portlights rather than deck hatches work for us as they can be left open when it rains.
I hope some of our priorites borne from our experience of liveaboard life help assist you in ypur choice of boat.
I am not going to mention sea keeping quailities as I think you already have than nailed. Best of look with your purchase
Have to agree totally with this post , I went looking for something that ticked all these boxes , thought firstly I would get away plus 40 foot but when started the hunt realised as blue water live aboards it was not big enough , ended up 49 foot Najad .... The points made in the post had to be taken into account , it is soon to be home and keeping Wifey happy and comfortable was high on the list ....
 
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