You should talk to O.P. He is the other resident T-28 nut. Here is his profile:
http://warbirdinformationexchange.org/p ... file&u=112
There are several T-28 owners, flyers and maintainers who frequent this board. Hopefully they can answer your questions. I've never flown in a T-28, but do have T-6 time. If you don't have any taildragger time, the T-28 might be a bit easier transition. Even though it is more complex than a T-6, it might not be too bad for you, since it sounds like you have some complex time in light twins.
BTW, I'm a firm believer that excellent training can overcome any type of experience level. Just because you are inexperienced, don't let that discourage you from getting the plane of your dreams. As long as you have the proper training from someone who is actually going to teach you how to fly and not just give you the rating or paper that says so, it will all work out. Just about anybody can learn to fly any type of airplane. It's just that some people pick it up quicker than others. Any instructor worth a crap, will keep giving you lessons, until he/she feels you are safe to fly it alone without supervision.
Another factor is the logisitics. Since you live on an isolated island, it might be difficult to find qualified maintainers/instructors and/or obtaining parts for it.
I'm sure you have already thought of this, but what you want is not going to be cheap at all! I hope you are financially well off.
Also, welcome to WIX and please contribute here! Thankfully, most everybody's contribution here is valued, and there doesn't appear to be the "elitist" attitude that seems to permeate a lot of internet forums. Don't think that because of your inexperience in flying that your contributions are any less valuable. Everybody with any interest in warbirds is welcome here!