FWIW, the situation with the twin otters on Cayman Air is mainly a fall problem. They only have 2 planes and they are over 40 years old. They need to be taken out of service periodically for maintenance that requires them to go off-island. They usually do that in the fall when travel to LC is much more limited due to everybody but LCBR closing down for hurricane season. If the one plane still on island breaks down requiring significant repairs, they have no plane left to get people on and off of LC.
During the rest of the year, if one plane breaks down or has to be taken out for on-island maintenance, they consolidate people onto the other flights. When they do that, it often means not all of the luggage goes with. I have never been on the otters when they were completely full and I think that is done on purpose. To my knowledge, they don't have refueling facilities on LC, so they have to carry enough fuel to make it there and back. So they typically fly partial loads unless they are passing through CB as part of the trip, in which case they can refuel on Brac. If they have to double up passengers on flights due to having a plane out, it means the extra passenger weight has to be offset by bags. The morning flights are usually less full and they bring the extra bags then.
I have been going to LC and CB since 1995 and have had luggage left behind by Cayman Airways once and by United out of Houston once in all that time. The Cayman bag was at my doorstep the next morning, while the United bag took 4 days to catch up. Cayman Airways does have an open RFP out trying to buy another used Twin Otter to give them three planes in the fleet. That would allow them to always have two planes available even when one is off island for maintenance. Apparently used Twin Otters for sale are not easy to find though, and for whatever reason, they do not seem interested in the newer models (pilot training requirements perhaps?). If they are able to source one, it could make a big difference in the reliability of their LC service.
