If we rely on this site in modern Greek, which in turn is based on the 9th century kletorologion of Philotheos, the quaestor at that time was responsible for judging cases involving wills.
Thus, a meeting between a quaestor and a wealthy merchant does not seem unrealistic. But I am plagued by the question of how the merchant may have addressed the quaestor.
Unable to think of a suitable text to answer my question, I leafed through Digenes Akritas, to get an idea of how important people (but not quaestors) may have been addressed. There, the ubiquitous appellation (in the original) seems to be ΑΥΘΕΝΤΑ, but the relationships depicted are mostly personal. The English translator of my edition believes that the epic was written in the 11th century, but emulated earlier language. The whole thing is mostly believed to be set in the reign of Basileus I or Basileus II, between whose reigns the aforementioned kletorologion was compiled.
I suppose that the appellation may greatly vary with time and context (inside/outside courtroom). But I would very much welcome any information or even the well founded assertion that titles such as ΑΥΘΕΝΤΑ, ΑΡΧΩΝ (or perhaps the more modern ΑΡΧΟΝΤΑ) would have been a good generic option.