For multi-disc albums, I rip each to a separate folder, usually with “, disc 1” or something similar appended to the album name. For multiple versions of the same album, I add a designation in parentheses to indicate the version. For example:
A Distortion Of Love (msfl)
A Distortion of Love (SACD)
Hell Or High Water (XRCD)
The nice thing about this convention is that Roon will show the version in the Roon UI.
Check for the pre-emphasis flag. This may be an issue on a minority of early CDs. If set it will mean the rip will playback with a treble lift. Best to use sox or similar DSP to correct the rip.
Rip a few boxed sets and compilation albums. See how they appear in Roon. Make sure you are happy. If you aren’t adjust the way you set metadata for them until you are.
Ripping to FLAC compression level 5 gives the best compromise between filesize and ripping time.
If WAV sounds better than FLAC on your system, or FLAC level 0 sounds better than FLAC level 5, get a better system.
As long as your rip passes the Accuraterip check there is no need to use anything but the fastest ripping speed. You only need to use the slower more intensive ripping strategy for the odd problem disc.
Don’t rip across your network. Rip to a local drive and then transfer stuff if you have to.
Watch out for very long file names - a possibility with some classical CDs.
Don’t worry about filepaths/folders if you are using Roon.
Before you start ripping, ask yourself whether you need to bother. Unless you have really obscure tastes most of your CDs will be available to stream from Qobuz or Tidal, often in higher than cd quality. So, if you haven’t, get a free Qobuz or Tidal trial before you start ripping.
Start with an up to date copy of dBPoweramp! I have a 4 year old registered version (16.x) and it seems to have lost the ability to retrieve metadata from most of its online sources. I discovered this recently after ripping the final few dozen CDs in the house (none left to rip now). As a result, I discovered that mp3Tag can retrieve metadata too.