If the DIP is doing the upsampling, then I think your DAC upsampler is only going to upsample if you're upsampling further - say to 24/192 (happy to be corrected on this). Otherwise, it is receiving a 24/96 signal and doesn't need to upsample the already upsampled signal. IMO the DIP only makes a significant impact in the situation where the DAC doesn't already attenuate the jitter (either by upsampling or reclocking in nnative resolution.
Of course, there is the option to buy the DIP combination which gives you the option to upsample with the DIP or just reclock and amplify the signal in native 16/44.1. Personally, I don't think you'll notice a significant difference with either an upsampling MSB or the upsampling Bel Canto as both these DACs already attenuate the jitter in the incoming signal. All IMHO of course.
Of course, there is the option to buy the DIP combination which gives you the option to upsample with the DIP or just reclock and amplify the signal in native 16/44.1. Personally, I don't think you'll notice a significant difference with either an upsampling MSB or the upsampling Bel Canto as both these DACs already attenuate the jitter in the incoming signal. All IMHO of course.