Welcome to the Orchid Board, and congratulations on flowering this plant so well.
It is a Dendrobium or Den., probably a hybrid. Dendrobium is a huge genus with species in many different groups, requiring different culture. This is in the Den. phalaenopsis or Den. phal. group, named after the flower resemblance to the unrelated genus Phalaenopsis. This kind of Dendrobium likes to be warm, well-watered and brightly lit all year.
The time to repot is when the plant makes new roots, and they are only 1-2 millimeters long. That is likely to be sometime next Spring. It is outgrowing the current pot. The old medium may have begun decomposing. Like most other orchids, it prefers lots of air at the roots. People often use medium to large orchid bark for Den. phals.
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