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Put the correctly named loot table in the correct folder. In this case the reason your attempts didn't work was because you put the loot table in {your_mod_id} directory not the {minecraft} directory. You have to make your chest block return the correct Resource Location. Look at the vanilla chest for examples.

You need to extend FontRenderer and override FontRenderer::renderUnicodeChar. The actual font should be added to the game as a PNG file; The ResourceLocation of said file is used when instantiating your own FontRenderer. You should instantiate it as final inside your proxy, and call the FontRenderer from your proxy whenever you need to use it. To use this different font, you merely use the stored FontRenderer instead of calling Minecraft::fontRenderer like usual (or the FontRenderer given to you if that's the case), and draw the text with FontRenderer::drawString or any of the other drawing options. If you have any further questions, I would direct you to AbyssalCraft's GitHub, as they use the Aklo font to obfuscate some text.