Hi, liron, and welcome to CF.
I hope you'll get a response from someone with direct experience, but perhaps my limited knowledge may be of marginal help to you.
I planned a November passage
from St Thomas to Marathon Key a few years ago, and was also concerned about having somewhere to "bail out" if weather
became a serious issue. My conclusion was that Ragged was too far out of the way, and the few small cays along the north edge of the Old Bahama Channel didn't look like safe options. I decided that I would carry on without stopping to Cay Sal Banks. If weather precluded crossing the Gulf Stream
there, I planned to anchor
at one of the two semi-viable anchorages
there--Cay Sal or Anquilla Cays. I researched various sources and holding is not the greatest, with currents and scouring, so an anchor watch would be prudent.
As it turned out, my weather routing service
advised me that a tropical wave was approaching from the east and a strong cold front was coming from the west. It appeared that they would collide over us when we were half way through the Old Bahamas
Channel. I elected to turn north through the Turks and Caicos
and take the weather in the open waters of the Atlantic, and was glad I did. We ended up proceeding past Eleuthera and through the NE Providence Channel, crossing the Gulf Stream
from Great Isaac Light to Hollywood Beach, which is just south of Ft Lauderdale.
You might want to consider taking that route
and avoiding the potential issues of the OBC.