There is quite active discussion on exactly this point you are bringing. Indeed, there are only few DAC’s which can do DSD without funky “interpretations”: Best native DSD DACs for use with HQPlayer? - Audio Gear Talk / HQ Player - Roon Labs Community
Yes, there are many combinations and depending on software settings, your chain, the DAC and your personal preferences it is possible to find combination that matches your tastes and viewes the most, both in HQP and in Roon. By the way DSD to DSD upsampling in HQP does not use filters, but rather Integrator + Converter + Modulator.
Also if you search this forum HQ Player section, if I remember correctly the question of benefits in upsampling DSD64 to higher rates, like DSD256 was discussed.