Cost and sailability
You need to decide on a price range. Then comes the big question how does the boat sail in all conditions. I say this based on the following, I own 2 boats a Lancer 36 and San Juan 23 and I crew on a Benneteau 411. It is the latter boat that makes me ask about sailing qualities. I have sailed the Atlantic in 45kt wind and 30ft seas in the 200K production 411. It has taken everything in stride from this to light air. Additionally, considering it has made 10 trips back and forth to the BVI plus is sailed a lot in the BVi and the Chesapeake, it has held up well. Before I bought the Lancer which was a deal too good to pass up, I was looking at the more upper end so called blue water boats such as HRs and Moodys. These cost a lot of $$. I would keep asking myself what if I bought one of these things in the 300-400K range and I found it did not sail as well as a 200k Benneteau. I have sailed on some boats that feel like they want to move though the water but just can't. This is in contrast to the Benneteau and Lancer that seem to glide through. I would liken it to rubbing your finger an thumb together with or without soft butter between them.The problem is how can you know? One way is to charter since I think it is hard to get a test sail on the new higher end boats. Even chartering what is the likelihood of seeing 45kts? Now with regard to the so called production boats its more like going to a car dealer. The vaguest interest will get you the offer of a test sail. There is one last possibility to see how a boat handles and that is maybe doing one of these adventure learning charters, e.g. mahina expeditions (www.mahina.com). It is on a big HR and you could pick the location/sailing conditions since the boat moves around the world. This is not cheap in the range of 5k, but I think if I were going to spend 300-400K or easily more for a Swan, Hinkley, or Oyster, it might be a wise investment. Lastly is this a retorical question because for 2 people I am not sure of the purpose of going much over 40ft. Things get exponentially harder to do and systems exponentially more complicated and expensive.