The fully Hebrew locale on the top line was all that it took! I have a locale set in my class and all I did was change it from what it was to Locale(identifier: "he-IL@numbers=hebr") and that fixed it!
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I updated the post, now all the dates are uniformed showing the same information. so with DateFormatter it shows ב׳ for 2 and תשפ״ג for 5783 and with Date.FormatStyle it doesn't show the numbers in Hebrew.
Regarding your second question:
DateFormatter will do it right in most cases, if you put the modifiers in the right order, but with Date.FormatStyle nothing seems to work
You have to click on the app name on the left pane (My App) and under capabilities add Network Connection (incoming, at least for now) I just had this issue recently and that solved it