1) I've been told that belts should always match your shoes - but what do you do if you have an odd coloured shoe (eg an ox blood or burgundy) and can't find a belt to match?
2) in regards to trousers - should they be cuffed? What is a good trouser height for suit pants which is both contemporary but appropriate?
1. If it's close but not exact, no one will notice. In fact no one will really notice anyway until you head to an SF meet up... Some shoe makers, like AE, sell belts to match their shoes exactly - might be worth checking you are paranoid.
2. SF really needs a "can of worms" emoticon.
The only correct answer to this question is "personal preference". I recommend looking at some photos of breaks/cuffs then taking one you like to your tailor.
Speaking of AEs, new boots on today (raising my middle finger to the hot weather...). Nothing like that "new leather" smell that follows you around when you put on a new pair of shoes...