CD ripper

To answer your questions:
Doubtful but possible.
And pretty sure you can’t rip to DSD and a google search supports that. The better question would be FLAC or WAV, a FLAC is compressed and a WAV is not. That answer really depends on the size of your collection and your storage capabilities.

You could rip SACDs to DSD. If you really wanted it, you could rip/convert even CDs to DSD but I am not sure what would be the benefit of that and it would cost you more. Rip CDs in one of the formats mentioned above.

Note: FLAC is supposed to be lossless. Those more knowledgeable may chime in about the differences when it comes to sound (FLAC vs. WAV, etc.)

I have over 10K CDs that I have ripped.  I just use iTunes to rip to aiff (only because the title mapping is easy).  I then transcode to flac with AudioRepair from XiVero.  Works like a charm and can correct for some CD errors.  Flac, aiff and wav are all lossless, flac files are just smaller.

Redbook files can sound amazing on a modern DAC.

EAC all the way.  FLAC is a lossless compresses format and the perfect end state ... WAV is uncompressed so just larger files for the same quality.  

If you have SACD discs you can rip an iso to DSD using iso2dsd 

I completely agree with EAC and the recommendations above. I have ripped well over 7k CDs this way. However, if you are looking for a fool proof, plug and play ripper that supports FLAC, checkout the Bluesound Vault II. It is a small footprint, about the size of a NUC, dead quiet and very easy to use. I had to get one to allow my wife to rip her copious CD collection as I did not have 4 weeks of free time to do it. It worked flawlessly.