Why upsample before modulation?
The reason is aliasing. Because the modulation is digital, on the discrete signal, the sampling frequency should be high enough that the channel's frequency band does not extend beyond the Nyquist frequency = sampling frequency / 2. If the sampling frequency is too low, the frequencies beyond the Nyquist frequency will alias to other frequencies, meaning that you would be transmitting at the wrong frequency. By lowpass filtering before modulation, you are removing spectral images of the baseband. If those are not removed the signal has frequencies outside the baseband and similarly the modulated signal won't be contained in the channel's band.