Learn me on some boats... please?

[jlcnuke]

So, I'm still a few years out (probably) from buying my boat to go cruising in, but I like to research things that interest me. As such, I've been looking into what kind of boats I might consider buying in 3-6 years (or at least trying to get an idea about the manufacturers, what size boat to look at, etc).

So, while I don't have great plans of circumnavigation (though I'm not against them), the idea of crossing the Atlantic from Europe to the Caribbean is slowly becoming something I may be interested in, in large part due to the number of boats that seem to hit my "wants" list over there. However, besides checking to see how many of those boats make the Arc in recent years I don't know much about them and for some don't seem to see too much info.

So, I guess I should first start off with my "wants".
1. I'd like a boat I can enjoy in the Caribbean, so deep keels aren't looking good from what I can tell (Bahamas tend to be shallow from my reading etc).
2. I'd like a boat that I can take 1-2 "sets" of guests comfortably along with. That means a minimum of 2 cabins, but three might be preferable (just so everyone can have some privacy).
3. Preferably, they could be set up to single-hand without too much modification.
4. Traveler not in the cockpit (I would just find that annoying and am not interested in boats that have them where I'd have to step over them to go from the helm to below-deck).
5. "Decent" amount of storage space.

So, looking online I see that Europe seems to have a lot more boats that "seem" to meet those criteria. Beneteau, Jeanneau, Bavaria, and Oyster seem to have the most boats doing Arc each year. Though some others like Elan etc that I've not heard much about (and seem to be mostly Europe based) are also on that list (I think a Harmony too).

It seems to me, and I could be wrong, that any of those could likely be used to cruise around Europe for a while after I bought (might as well if I'm there, right?), then sailed over to the Americas to go cruise the Caribbean. Obviously I'd need some crew for the Atlantic crossing (and by then I'd expect I'd have a decent amount of sailing experience myself as well) but that's another reason to think it would be a good idea to have a couple/few cabins in my lay opinion.

There are a few things that I see as concerns:
1. Provisioning - making sure the boats can be/are set up to support a crossing.
a. Safety stuff and comms obviously, but also adequate water supply (watermaker preferred/needed?).
b. Power needs - enough fuel to run the engines often enough or need to outfit with solar etc before crossing?
c. Adequate food storage - I don't really think this would be an issue, but could be if storage on those boats is too limited?
d. SSB or sat phone probably necessary and generally not included on most boats from what I see?
2. Would a boat that could support crossing the Atlantic comfortably be too much to enjoy single-handing around the Caribbean?
3. Would it be too hard to get crew to come along for the journey? I'm not interested in paying a captain etc to do the journey, but I'd be interested in finding some fairly experienced sailors who'd like to come along for the journey (paying for their own transportation to/from the boat and their part of provision I'd guess wouldn't be unreasonable but I could be wrong there to?).
4. Former charter boats okay or are they "avoid at all costs even if free!"?

I know someone's going to ask about price point, so I'll say that I've been looking at boats up to about $75k asking and see 2-4 cabin boats in the 38-47ft range on yachtworld.com etc that "seem" to meet my wants.

Yes, I know that many of these questions have been addressed separately (at least in some similar form), but I didn't see any threads in my searches that discussed specifically the questions/concerns I have so I figured I'd "ask the experts" here .