Seriously considering purchasing a new Mini and always get the best info from sites like this...so here goes. Apologies if these are stupid questions...

Considering either a Clubman or Countryman. The countryman seems more practical, but the Clubman speaks to me. If I do the Clubman I will probably do the Hampton edition in Pepper White. The countryman will be either toffee or royal gray. So here are my questions...
1. Pros and cons of leather versus leatherette...besides the obvious cost? The Hampton is leather of course, but if I don't go for that, is the leather worth the extra one or two grand? Does Mini leather wear well?
2. Is there room to deal off the sticker prices? Does all the dealing and trade in negotiation happen before the Mini is ordered?
3. Relatively speaking, are Minis expensive to insure? How about to maintain?
4. Any options I should definitely spring for? Planning on nav and the panorama roof for sure...will definitely be manual tranny.
5. Anything else I ought to know?