Paulo, you don't disappoint! You were right in your assumptions of what I'm looking for nearly across the board. I would say that I am very partial to twin rudders and prefer a tiller( or twins), but could more than live with the Elan 350 set up. When you stated adding a large cost to refit the Akilaria, what else would be required other than what is considered "sail away ready"(electronics included)? I agree it is Spartan, but although I have yet to sail one, it looks pretty well suited to 2 or 3 adults for extended time aboard. I agree on the Pogo 10.50 -beautiful but a bit of a white elephant. The A40 is very nice, but I question if it may be a bit too large? From your previous posts, I see that you are a big fan of the Elan 350 as well. I have seen more than a few listed as "sail away ready" for sub $200k, but again is that lacking in necessary equipment? Essentially what I'm asking is what would you look for if you were in your early 30's, single without children and had 2 or 3 years to sail as much as you wish where ever you wish? Thank you!
First of all, I have my preference for the boats you outlined but I won't go there.
You should think about seasons and weather / temps you want to be sailing, moored, anchored or docked at. This will have a bearing on the creature comforts and interiors you should be looking for.
2nd, I'd suggest thinking about where you want to cruise - little if any tide swing in the Med, different elsewhere. Do you need a boat that can beach or are you fine anchoring a half mile off the beach ;-).
3rd, how many days / weeks you plan on going without topping off at the docks?
4th, how may people will join you and what time of comforts are they looking for? It's one thing to be a single bohemian... another to expect all guests to do likewise if you want to see them more than once.
5th, why 3 years? That's a very, VERY long time on a boat for about 99.999% of the world population. If it is 3 years non-stop, day in and day out, I'd suggest going with a "comfortable pair of shoes" as opposed to those pocket rockets. A nice compromise is the RM 1050 as has been seen previously on this thread. Other cruisers will give more comfort for the day to day that is more than a "nice to have" after a few months non-stop.
On the boats listed, you have a 2X price differential. Can pick up a very good condition SF2300 for around 75K€ ready to sail. An Elan, Akilaria, or JPK (960) for mid 150K€'s ready to sail, or a Pogo 10.50 but not under 200K€ ready to go outfitted with what you need to do what you're planning on doing. There is no used market for the 10.50 now as owners like them too much. There is the A35 which is a smaller version of the A40. It is a fast, light boat that works well everywhere, but I wouldn't want to live on it for more than a few weeks max. I haven't been on an A40, but the interior looks the same and again, not something I'd initially look to "live" in. The A's do have amazingly light feel on the rudder and are fast, very well built boats (I've races the GS and A31) but they aren't live-aboards in my opinion.
Everything's a compromise so take 20K of your 200K budget and rent for a week the target boats you're looking at and I'm sure you'll find something that works for you.
Good luck and see you out there in the Med some day!