I would hem a couple inches and then cuff it an inch. But that's just me. Too much stacking looks awkward imo.
Belts is all up to you.
If you get a natural-leather belt, the more you wear it, the more it will "patina".
That's the before/after of a Naked&Famous belt. Tanner's a popular choice for quality leather too.
Personally I don't care enough to have a fancy belt. I've been rocking a plain black Levi's belt for almost 2 years now lol