This (can be) a pretty involved topic in so far as understanding the two different formats and especially upsampling in the correct context, since it (upsampling to DSD) is actually fixing / addressing inherent distortion
"Most" DAC’s that use chips (ESS Sabre for ex) as well as CHORD, upsample everything internally and almost impossible to avoid (there are some exceptions and depending on how the DAC designer implements the "chip" can disable certain functions). So the comment above about "cheaper equipment because the upsampling algorithm is basically filling in holes" and "Therefore the upsampled music is not true to source" is incorrect IMHO.
NOS DAC’s (Holo, Mustec, T+A, last gen Lampi’s) are just that and there are a fair amount of NOS DAC’s available nowadays. These are a prime target for umsampling prior to DAC and a widely used method at this time is HQP. Its a great software with many filters and modulators for both PCM + DSD. The developer is all about DSD (upsampling PCM > DSD and native DSD is HQP wheelhouse) and "usually" best if installed on its own dedicated wkst. If using roon (for lib mgmt and sending to HQP), keeping roon on its own dedicated core wkst is a good idea.
The format hi-res is really irrelevant and is used incorrectly in a lot of topics IMHO. It all has to do with provenance > the masters. There are a lot of great redbook sounding CD’s as well as a lot of crappy sounding re-masterd and upsampled and sold as hi-res from same CD.
If the master / recording was done natively in a higher rate (24/96 for example) or DSD, that’s great and more then likely it will sound very good (or as best as the mastering). My point is the bit rate isn’t automatically the end all - you have to know where it came from (to be absolutely certain). I would venture to say many artists now record in 24/96 and very few in native DSD.
DSD IMHO is anything but hard, brittle etc.. and generally speaking my fav format especially on a DAC meant for it.
The use of the new HQP EC modulators and upsampling to DSD 256 is pretty ridiculously good and I upsample everything to DSD 256 or 512 with the orig modulator.
This is all really to say, there is no right or wrong way to go here and comes down to personal preference and ones system.
If you have a solid wkst you can run HQP on with a quality USB card to go DAC direct OR send HQP to an NAA (opticalRendu, Pi, NUC, Fillet etc..) your golden. Additionally, you can now very easily get HQP in an embedded version (custom ubuntu with HQP installed) OS image. Just burn it to your internal M.2 or boot to a USB stick.