You can do some via Costa Rica and Bermuda but the restrictions, cost or availability of flights are all deterrents.
The MHD is the best value bar none and has availability across many carriers to many destinations with generally a choice of several flights per day.
e.g. YYC-SJO is $2300 in J and allows routings via YYZ. I can do the same thing via MEX for $1700 or PVR for $1300 in J, with more available flights per day.
YYC-BDA is $2400 in J.