Moving to St. Thomas in Sept. should I keep my 2006 Toyota Tundra limited or get a 4x4?

Step 1: Ask wife.  Happy wife, happy life.

Step 2: Do what wife asks, if she doesn't care......do whatever you want.......get the 4X4.

@jaldeborgh she likes the truck we have, but I was asking as a safety issue. I hear the steep incline and sharp turns. maybe something a little smaller with a 4x4 would be safer with two children.

I’m not too familiar with STT roads, other than driving between the airport and Redhook.  I will say a 4X2 on STX is fine, if you stay off the unimproved roads, but my sense is STT has more and steeper hills.  I’ve also driven all over STJ without any real issue in several different rental cars, again as long as you stay on the paved roads.  We did rent a house one year (on STJ) where the owner strongly recommended we have a 4X4 vehicle, he was right, but the house was on top of a steep hill with an unpaved access road, we were glad we rented a Wrangler that year.  We currently have a Jeep Cherokee Trailhawk (on STX) which works well for us as we now own a home at the top of a steep dirt access road, but it’s not a pickup so that may not be right for you.

The pattern emerging here is that if you want the flexibility to navigate/explore/live off the beaten path you might be more comfortable with the 4X4.  I’m also confident that a 4X2 along with a little common sense will work just fine.

My wife and I have had little difficulty adjusting to driving on the left as well as navigating the roads on either STJ or STX.

I recommend getting a 4x4 or an awd.  You aren't always going to need it, but when you do you do.  There are a few spots on STJ that I wouldn't drive to/on in the rain with only a 2wd.  And with two kids, the peace of mind is worth every penny.   Toyata Tacomas are very popular on STJ.  And the resale value on a 4x4 truck here is pretty good so it's not a bad investment.   

Whether your wife will need 4 wd is going to depend on the housing arrangements or her propensity to go to deserted beaches.

I can say fromexperience if you bring a Tundra and find out you want a 4x4 vehicle you will be able to sell the truck for much more here in STT than wherever you are there.

thank you so much for all your comments.