Let's infuse our milk, in a pot add milk, butter, anise, and other aromatics, sugar and let it infuse in low/medium heat until it's about to boil then let it chill.
Start the caramel, in a pan add sugar, water and let it cook till you get a brown(not black) thick texture, then pour it into a cake mold. (I used a 9x14 inch cake pan)
Once the milk chilled, strain it. Then submerge your bread into the milk, add once egg at the time, integrate your ingredients (use a hand mixer if possible), add raisins, rum pour the butter to your baking pan and bake it in a preheated oven at 350 F / 180 C for 45 - 60 min in a Bain Marie.
For the chocolate glaze add ingredients to a pot then let the chocolate melt and integrate with the condensed milk, use while hot add cream if is too thick.
Notes
Best tip to make caramel is patience, let the heat do the work, do not use a spoon or anything just let the sugar melt, do it at medium heat, patience is key for a great caramel