You posted in the Mac Pro (desktop) forum, but your question is better asked in the MacBook Pro (laptop) forum.
I can only offer my advice on question 4: I think you'll be fine purchasing a MacBook Pro in January, I'm buying one myself for my wife in December. I don't expect any major upgrades on the MacBook Pros for a while (just my uninformed guess).
As for your other questions, I don't use a laptop, so I can't answer confidently.