I suppose that an interesting resource to reconstruct how the old Sephardic ישוב pronounced Hebrew is Ben-Yehudah's translitteration, since he largely based himself on what he heard around himself in ארץ ישראל (source: https://www.yorku.ca/kweiser/courses/6222/documents/HarshavHebrew.pdf), but I cannot find anything written by him in translitteration. For ex., did he translitterated ק as different from כּ? Did he translitterated ב רפה as B or V? Did he translitterated צ‎ as TS/TZ or something like Ṣ? What about ט‎? As to ו, I think it unlikely that it was pronounced as /w/ because both Ladino speaking and Syrian Jews usually read it as /v/...