Question #1:

Your TFSA does not reset. If your 25,500 shares are now worth $8,000 for example, selling those shares then taking out that $8,000 would then mean that you have room of $8,000 in the coming year (you have to wait till the next year) plus the yearly TFSA increase allotment of $5,500 for 2014 giving you total room in 2014 of $13,500.

Question #2:

Yes, if you buy within the 30 (calendar) days, it is considered a superficial loss. The superficial loss is added to the adjusted cost base of the repurchased or substitute shares. When the repurchased or substitute shares are sold, the loss can be claimed (if they haven't increased such that their is no loss). In terms of settlement date vs actual sale date, I haven't seen any discussion in that area, so I would assume the later date to be sure. I imagine you can buy on the 30th day.

Of course a superficial loss isn't the end of the world, you are just denying yourself of a loss today which you are still likely entitled to at a later date.