Retiring to San Pedro this year...what are the approx. annual costs of insuring a Golf Cart / Skooter / Boat, plus necessary permits ?

Suggest you contact insurance carriers for quotes - they seem to change over time.
Generally speaking -
Golf cart insurance is very cheap ($100 or so a year for our clunker). Would assume scooter is similarly inexpensive.

Boat insurance - I think it's around 2% of the value insured.

Boat license fee is around $100 a year.

Annual golf cart fee - inexpensive.

Permits to bring a land-vehicle to the island are not so easy to get - suggest you look for something already here.

I just brought to the island a motorcycle and it was about a months worth of visiting the town board waiting for a committee to decide whether meet or not meet with 7 pages of application, three stickers, insurance and a plate. Total cost aprox.700.bz + 150 barge fee.
Photo of where you plan to park it at home and another of where I park it at work was about the most ridiculous...no thats not true the sticker that no one could explain was the most ridiculous.
I ask the lady what is this for and she said, "To stick on your motor cycle!"
Be patient and keep a good sense of humor!

expect to have QRP status at the time of our move...
thanks much for the reply

Although the QRP allows a vehicle to come duty free, the permit for either SP or CC is locally controlled. Both places are hard to get permission for a vehicle to land. Even temporarily having a vehicle on the cayes is hard to get.

Take it from me that QRP means absolutely nothing to the locals on AC. I know as it cost me about $10,000 USD. Don't believe anything anyone tells you either. Just put your head down and jump through all their hoops and there is a chance you will get a permit. The last time when I renewed I was questioned about the aluminum box on the back of my Ranger and some mumblings about the permit not being renewed because of it. It is simply disgraceful.

Oh and I bought some lights for the soccer field as per one of the local politicians as that was supposed to help the permitting process - It DIDN'T!

Three classes of insurance for private homes:

1 all concrete/block, walls and floor slabs
2 concrete slab and pilings (if raised) with timber framing.
3 all timber.

Cost per $1k insured on the Cayes:

1 $12 per
2 $20 per
3.$31 per - many won't insure this type at all.