Roxbury--It sounds like you made the smart choice for your comfort and conditions.
Since reading the "recommended" routes I asked a few local sailors' opinions of going CCW vs. CW and most said "depends on the wind" and that it would seem odd to have a "preferred route" unless that "preference" was based on predicted winds during the charter period. One thought was that as people leaving Moorings or Nanny Cay may not be fully familiar with their vessels yet, they have more options on the south side of Tortola to "pull in" then on the the north side especially if things are not going well. Support from the charter companies can also get to the customer much quicker and stay in radio contact on the south side when there are problems.
One thing that recurs frequently on the radio is calls for missing dinghys. These aren't stolen but have come loose from charter boats while underway. To all that charter "make sure you dingy is attached and still behind you"!!!! My wife and I have picked up a couple of lost dinghys in Drakes Passge and over between Trellis Bay and Guana Island. One was recovered by the embarassed and intoxicated couple shorty after. The other was picked up the next morning on JVD from a Sunsail Rep.