This can be done. Please see the section in the FAQ titled “Can this recipe be made in a regular loaf pan?” for all the details.

I wouldn’t add additional liquids. You might be able to swap the milk with buttermilk, however the acidity in it could change how the other ingredients perform. As far as orange juice, you might be able to use it in a glaze and drizzle that on top. But adding it without changing the other ratios would make the batter too thin.

So – for the sugar. It says 1/4 cup for the tops – of EACH loaf. So yes, the measurement in the recipe card of 1/2 cup is correct. You divide between the tops of the loaves. But really – it’s not super critical that it be exactly. You can use what looks good to you when adding the topping layer. The sugar is listed separately in the recipe card – first for the bread, and then for the tops.
I don’t recommend using dried cranberries. First – they are already soaked in sugar so that will alter the flavor. But you also need the moisure content of the whole, fresh cranberries – otherwise the end result will be disappointing. I have not personally tried it. But I would say that if you absolutely have to – soak them first so they pulmp up. Just keep in mind that the end result won’t be as amazing as it could be.

I haven’t tried it – but I think that would work fine.