1. How do you know how many times you have reloaded a case....I keep mine in batches, same head stamp, same life. I store them in 50 round ammo boxes. I have load labels that have 1 thru 15 printed on them and I just cross off the last one I loaded. So, if 1 thru 5 is crossed off, I know I have loaded them 6 times. The load labels have other important info on them as well, such as what bullet, what powder and how much, what primer and OAL.
2. There is many, many ways to anneal cases. I have found the Hornady Kit is easy to use and do. I anneal with a Hornady Anneal Kit #041220. They come with 3 spinners (for different size cases), Temperature Indicating Liquid (TIL) and instructions. I use the TIL to indicate the correct temperature. Once I learn what the case looks like when it reaches the correct temperature, I do not need the TIL. I bought a inexpensive Black and Decker battery powered screw driver to run the spinners with. They recommend 180 RPM and the screw driver runs at 200 RPM...close enough. The spinners have a hex drive shaft that fits right into the driver socket. Once the case gets up to the correct temperature, I simply tip down the spinner and drop it into room temperature water to cool them off quickly.
http://www.midwayusa.com/product/360902/hornady-annealing-systemIt is not cheap, but will pay for itself as soon as you save 200 cases or so by annealing them.
Good Luck and Good Shooting