The possibility of exploiting heterogeneous quantum systems to high precision, for storing, processing, and transmitting information, makes them ideal candidates for multitasking purposes in quantum communication. Appropriate quantum systems involving a judicious choice of interactions that augment each other are potentially useful for probing deep into quantum regimes. Here, we use one such hybrid bipartite quantum model, with one subsystem made of a pair of qubits and another comprising a pair of oscillators, to study the entanglement dynamics and the entanglement transfer between discrete and continuous variables. The basic model is the standard double Jaynes–Cummings model, which, under suitable conditions, is known to support both entanglement transfer and entanglement sudden death. In this work, we generalize this model to include further experimentally relevant interactions, such as the beamsplitter-type exchange interaction between the oscillators, and dipole–dipole and Ising-type interactions between the qubits. The way various interactions and initial oscillator states affect the entanglement dynamics is examined theoretically for generic experimental conditions. Using exact analytical solutions, we show that, compared to the beamsplitter or dipole–dipole interaction, the Ising interaction can have a significant positive impact on entanglement sudden death and birth, and the postponement of the onset of these phenomena, apart from producing a substantial reduction in the time duration of the death.