Moving my cat from the Caribbean to Cape Cod

I divide my time between Bonaire and Cape Cod. I had 6 cats but have one left. Alfred is the last of the litter and is a healthy happy 12.5 years of age. 

When I am away from Bonaire, either my neighbor feeds him daily or I have pet sitters/renters at the house. Everyone loves him. There are a few times a year he is alone for a few weeks when the boy comes over to feed him.

Alfred has always been an in and outside cat. He has used a litter box a long time ago but now, goes in the yard. He hunts at night (I have a huge field surrounding my yard and by day, sleeps on my bed. He has a nice life.

I often think about bringing him up to the Cape. It stresses me out to think about it due to the flying and having to put him in a kennel for 12+ hours and take him out for every security check. 

Then, will be be happy here? My Bonaire dog is here and they loved each other. I also have semi feral (or abandoned stray) Blanku now who is also a male.

Opinions are welcomed.

Who would watch him when you are in Bonaire? Where would he get to see more of you?

Would he be an indoor/outdoor cat here? Is your area safe from predators? That makes me leery as I have a cousin that lives in Falmouth that lost his cat to a coyote last year.

If he leaves Bonaire, he'd see me more. I am in Bonaire 10 weeks a year. He would have to be inside due to predators on Cape Cod. Not sure how he'd love that.

His entire 12 years he has been cared for my pet sitters as I have always gone back and forth.