I'd say as soon as you've got a stable windows install running you can start, but the best CPU temperatures won't be achieved until the TIM has set up properly.
When you have finished reading this post you can start overclocking.
The first thing you need to do on your overclocking quest is to read the stickies on here and other forums as they're an invaluable source of info. Print them off as if things go wrong you may find a solution in there that can help.
In answer to your other question - the paste should last over a year if not more aslong as you dont remove the heatsink - in which case clean it off and replace with a good quality thermal compound.
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