The one in your pictures is the 26X as opposed to the other Macgregor 26 sailboats. There are a couple of those around here where I keep my boat.
My impression of them is that they are basically a power boat
with a sailing rig stuck on top of it. In that regards they have the ability to sail, but primarily would handle most situations like a power boat
So with that in mind I think you would find cross seas or quartering seas much more uncomfortable in a Macgregor 26X than a dedicated sailboat of the same size due to it's underwater profile and hard chines. Also, the sailing rigs on the ones around here, which I believe are factory rigs, are quite light in their construction so I doubt they would handle much of a pounding. So you'd probably have to drop sails
and become a power boat in situations with higher winds and waves such when you're away from your home waters and you can't risk something failing.
But the good thing is that they are fast like a power boat under power. One of the ones around here (maybe both?) have a 50hp outboard
motor and can travel in excess of 20kts. So that would make getting to and coming from the Bahamas very fast compared with a sailboat, and there are plenty of small power boats that go between Florida and the Bahamas.
As far as a 26 foot boat in general, living aboard
would be cramped for extended travels. I've sailed a Cape Dory
28 on week long ocean trips and when the weather is rough and you have everything jammed into the cabin
so you can get around on deck
to handle the sails you wish for more space. In port where the stuff can be left on deck
and the dock
and such you forget how cramped it is at sea when everything you have has to come with you. And cramped is somewhat dangerous because if something bad happens you don't want to have to move a bunch of crap to get to what you need to get to, on deck or in the cabin
. That's why I bought my larger boat. The Cape Dory
28 is a strong seaworthy
boat, but it's a whole other world when everything has it's own out-of-the-way storage
Like it was said earlier, it's all about your comfort tolerance.