Well, I just spent way more time than I had looking at attempts to ttf-ify various transitional Hebrew scripts, as seen in texts from periods relatively close to the time of Christ. I was unsuccessful. I suspect I'm merely font impaired, because the texts DO contain all the letters, but the fonts don't appear to.
If you're interested, look here:
http://www.historian.net/files.htmSome are not Mac compatible, and I haven't looked at those at all. I fiddled with the Pesher Habbakuk one quite a bit--using it requires some fiddling, as the creator notes--but I just can't find two of the letters necessary.
Other than that cool and kind of esoteric stuff, you're basically looking at modern Hebrew; the letters have not changed unless you want to use a variant script like the paleo-Hebrew Micro posted or the various later scripts developed for differentiating among blocks of text, which kind of look cool, but would be seriously anachronistic.
Heck, a nice-looking approach would be to use the forms used by scribes in hand writing sacred texts. The strong blocks with thin crowned points could work very well in a tattoo. I did not find a free font for that form, but they are out there. This form can be trickier to use as a font because they usually have options for multiple sets of diacritics, one of vowels and one of cantillation notes. Again, the letters look basically the same from set to set, just blockier than earlier versions and with the distinctive crowns on some letters. Also anachronistic. You'd be using the letters as developed by the people who consider themselves the heirs of the pharisees.
Personally, I would go out of my way to adapt an older scribal form like the ones linked to above. The necessary letters are in the images he posts, but don't seem to have made it to the font itself. Very odd, or perhaps it's an OS issue and they are there after all; I have several keys that show up as Latin characters. I'm haven't switching to another comp or trying to disassemble a jpg for this project--but if it was my shoulder, I would. Historically, it fits better. But then I also have some reservations about the association of relatively modern things being associated with the Jews of Jesus' time, because of the massive developments that both sides have made in the past many generations
In any case, I did type up four variants in a basic font. The second word is the same for all. The only difference between Hebrew and Aramaic, by the way is pronunciation, which is not indicated in the text.
The first word I put four variants--The messiah, Messiah, Yehoshua, and Yeshua. Personally, I haven't heard JC referred to as Yehoshua, but others seem to have. I also include the Yeshua version in a different font.
Trouble is I don't particularly want to post this online anywhere associated with me, so let me know if you want it and if so, how to get it to you.
