Neither of these boats is suitable for real blue water but the Endeavor is the better built boat compared to a 1995 HunterCC. Note...my opinion is on THAT particular boat in THAT time period and not all Hunters. If you want a blue water CC boat in that price range I suggest you look at Brewer42, Whitby42, Hylas44, Pearson422 and the Bristol 41 or 44. Understand that the AVERAGE condition boat from this era will require approximately $30-50k in maintenance and upgrades to be fully cruise ready so factor this into your budget.
I am a fan of CC boats and I think that the 40-45' range is ENTIRELY appropriate for your plans and disagree completely with the notion that it is too much boat for you to handle if properly fitted out. Just learn to sail it before heading out too far and you will find it EASIER to handle at sea and safer in trade winds and bigger seas than a smaller, lighter boat (generally). It will also have more stuff carrying capacity and live-ability at anchor.
I do disagree completely with your limitation on draft which will limit your choices, reduce performance and force you into boats that are more unsuitable for sea duty. You might consider a centerboard Bristol if the draft thing is such a big deal to you. I suggest a 6ft. limit if the ICW and Bahamas are in your plans.
As Anthony suggests...a 44 ft. boat has a lot higher ongoing cost associated with it compared to a 35' boat...Once initial fit out is complete, I would guess about double...maybe little less. Be sure you can afford it or your cruise time will be limited!
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