Again this is the kind of thing that would require supplementary approval(s) from the original artists, whereas reissuing original albums is relatively more straightforward, so for that reason alone I don't think it would happen.
There's also the issue that there aren't that many artists in the Sony and UMG quad repertoire that have enough releases to assemble a "new" greatest hits comp, especially when you remove the ones that are "unlicensable" for one reason or another, like Santana (being done by Sony Japan) and Barbra Streisand (owns her own masters), etc. I think most quad collectors are completists anyway and want the original albums (which is the avenue D-V have pursued) and not cherry-picked selections from them - not to mention the fact that the D-V discs are so affordably priced, you could (for example) buy all of the Guess Who releases and compile your own Greatest Hits compilation for less than the price that the old Audio Fidelity Best of The Guess Who SACD goes for, and not only would you have money left over, you'd also have a better-sounding set of tracks.
Speaking of which, D-V has reissued several "greatest hits" compilations originally issued during the quad era, including Best of The Guess Who, Vol. II (all-new mixes by GW engineer Brian Christian), The Best of Lynn Anderson and The Best of Henry Mancini Vols. 1 & 2 (phenomenal sound and content), as well as several Paul Mauriat titles which are compilations of some of his best-known work.
