Would anyone familiar with the different places to live in Saba be willing to share any pros or cons of living in any of the different villages? Thanks.

The Bottom: Close to the school. Close to the electric company, phone company, stores. Hotter there than other towns.
St Johns: close to the elementary and high school if you have kids. Great views. Not as much rain there (a minus).
Windwardside: close to the banks, stores, places to eat. A little more rain. No real downsides.
Booby Hill: great views, close to Windwardside.
Hells Gate: lots of apartments/houses. Close to Cove Bay for swimming and the airport. Great views of SXM and Barts. Farthest from the school.

Thanks for the info. If I am bringing a family (wife and 11 year old son) and will not have transportation for at least a few months where would you recommend trying to get a place at?

I would suggest Windwardside. All the wives try to get together at the playground with our younger children twice a week. But even if you don't have younger children, it is at least a place to talk to others. I have heard that there is a family coming from Utah with an 11 year old, is that you or maybe someone else?? There is a family here with a 12 or 13 year old son also. Anyway, Windwardside is very central, Booby Hill is only a five minute walk and same with English Quater. Hope this helps!