This is going to sound dumb...

We have bought a goodly amount of stuff to donate to st Anthony's. clothes, toys, etc. the bag is heavy now, and my wife asked me ... Why not just ship it ahead of us... Is this possible? It seems I read somewehere that this is more of a pain than it would sem.

I am not worried about the baggage on the flight, we get two bags each + a carry on + a personal item each, it is just turning into a lot more than I anticipated for the extended trip this time around.

Either I have never paid any attention, or just been in such a laid back fame of mind, but I have never seen mail being delivered like we have in the states.

It's possible but a royal pain in the butt and costly. If you can split it into a couple of bags and bring it, I'd do that.

Shipping would probably be extremely expensive. I once mailed a 6 pound package and it cost $69.00 US.

dont take everything...take it over a couple of trips or ask ppl to takes some for you..

We only get to really go once a year due to work constraints, the cost is not such a big deal, if I don't have to hump it down there. Would direct ship to my hotel be an option? Like DHL, UPS or something like that?

You would end up having to deal with customs...and your luggage would have to be picked up in Kingston or Montego Bay. Shipping charges, custom charges etc would be involved.
Maybe contact Gail from the Treehouse or the Wellington family from Travellers if you would like something shipped...they have programs set up for just this type of scenario.

I am taking my luggage, Bnewb. This is really for the saint Anthony's bag. We extended our trip this time around, and the wife is a heavy packer. I am starting to think it just might make more sense to eat the extra airline charge and hump it along. It's only going to be one way, and the bit of research i have done this evening for charges make me think it might be cheaper to pay usair.

Yup, I understand Hussyband. But, you're right....it will be much cheaper to just fly with it...or at least the same cost & less inconvenience...