Yes inflatables do get punctures and you will be constantly worried about them. You'll put out an anchor to hold your dingy off a dock so it does not rub and get a hole. Our puncture came fro a concrete dock in Guadeloupe.
You mention "an eight foot fiberglass dinghy". The four things you need to consider are: (1)Weight. Some of those things weigh a ton and would be very difficult to get on deck for your passages; (2) How dry is the ride; (3) How stable is it. We had friends with one that we named "tippy canoe"; (4) How large an engine can it take. Remember, at least 10 hp.
You mentioned a couple who wintered in the Bahamas with an aluminum dingy. I always thought the ideal dingy for the Bahamas would be an aluminum deep v fishing boat (the kind Sears sells). You would carry it on deck across the Gulf Stream and then you could tow it the rest of the way (you might put it on deck again to cross the Tongue of the Ocean). These things are cheap, indestructible and give a dry ride. Assuming this couple spent most of their time in the Abacos or Exumas, this would be ideal. It would be perfect for crossing Elizabeth Harbor in Georgetown.
We are agonizing over whether or not to purchase an electric windlass. If we buy this item, we'll need to cut out something else... We currently have a Simpson Lawrence manual which is in good condition. Our primary ground tackle consists of 200' 3/8 bbb chain backed with 300' 5/8 nylon, on a 65 lb. CQR. We've done local cruising using this set up and I've found no problems or difficulties hoisting - since it is two speed - in up to 50' of water. That is the background, here's the question:
You mention an electric windlass in your articles and the fact that you would expect it to "break down at some point".
Yes, it did break down. I'll cover it in our article on all the stuff that broke.
I probably would not cruise with a powered windlass (electric or hydraulic). I would make sure it was mounted in such a way that servicing would be easier than the one on "Down Time". Remember windlasses are on the bow and are constantly getting drenched in salt water. Sooner or later some seal is going to leak and you are going to end up with a ruined motor and bearings.
If you do decide to replace your manual one, get a horizontal electric model. That way everything is accessible from the deck.