The diurnal range. Difference between day and night temps. Cooling off at night indeed is needed for many orchids to set blooms. A dormant period during the winter months is needed for many of the dendrobiums. The combination of cooling off and staying dry over the winter months sets new roots new shoots and BUDS. In the Caribbean you have no much winter and the plant is perfectly happy to grow and thrive.
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Being close to the equator your diurnal range is going to be slim. Where as being farther from the equator provides a much wider range of temps. For example Jamaica has an annual avg diurnal range of 3 degrees. Malaysia on the other side of the world has an avg range of 23 degrees. Thier dry season is from May thru september. Your dry season is early in the year january thru february.
You have to accommodate and adjust your culture some to get the plants internal mechanism clicking for you. Know what the plant is and what its needs are and gauge that against what you are giving it and you can realize very rapidly whats causing your issue. Its not easy sometimes to get to the bottom of it but it if were easy we would have found something else to do.