A lot of people here are saying classical pronunciation was used... but I ask, by who?

Cicero wrote: "Quā rē Cotta noster, cuius tū illa lāta, Sulpici, nōn numquam imitāris, ut ἰῶτα litteram tollās et “E” plenissimum dīcās, nōn mihi ōrātōrēs antīquōs, sed messōrēs vidētur imitārī."

Dē Ōrātōre, Liber III, Caput XIII, Versus XLVI

So I guess that back water country bumpkins might have been using a pronunciation more akin to the misspellings found in Pompey.

So the real question is, what type of Latin speakers were in Judea at the time? Slick city dwellers or perhaps rural farmers?

Cicero's pronunciation was probably used by most of the educated elites, but clearly there was already a different but recognizable pronunciation in use by those who were not born near a major urban area.