A good test is to see if a modern Israeli can read Hebrew text of that period.
As it happens,, with a text from a Dead Sea scroll on display at the Jordan Archaeological Museum in Amman:
The Hebrew script at that time was closer in its style to the original Aramaic, with highly serifed letters which individually would confuse a modern reader, but when seen together, in context, is fairly decipherable.
Today’s Hebrew script more closely resembles the style developed in theof the 10th century CE, where the serifs are much more muted in favour of thick horizontal strokes, but a first-century Judean would fairly quickly acclimatise and perhaps even like it.
As Ayelet points out, he would be stumped by Modern Hebrew Cursive, but once it is explained to him that this was developed as quick, one- or two-stroke versions of the printed letters, he could master that, too, reasonably quickly.