SJU and WINAIR or LIAT, Eagle pulled out and Winair took the same stupid time slot as dictated by AEagle, making no difference whatsoever at all. LIAT departs an hour or so later so you could do it if you wanted to, go though SJU, i'd rather swim.
Jet Blue or whomever to SXM and AirBVI http://www.gobvi.com - avoid SJU altogether and can be done in a day if those on the west coast of the US don't mind red eye flights, no code share with Jet Blue yet, so you have to book on their site,
Out of Canada, ANU or BGA or SXM then LIAT (or air BVI) , give yourself at least 3 hours between flights in ANU or SXM, This will ensure your bags move across the tarmac either by themselves or carried in the former two.
Latest update http://www.citairways.com/ This was spoken about many years ago (2004/5) as a carrier for Ross U students, I'd met one of the owners and told them that Ross would be the tip of the iceberg. If people are traveling when Ross season starts/stops, then I forsee issues with people being bumped for students whining about no seats, but im an optimist.
In anycase, we remain one of the top 25 least visited places in the world, and of course the hardest to get to in the Caribbean. But once you're here, it's worth it....