what type of microcontroller are you using?
i have never taken any sort of anti static precautions with either AVRs or PICs and the vast majority of times i have fryed a microcontroller it has been because of some sort of short circuit.
as for the repeated programming, the datasheets for your microcontroller will tell you the exact number but you should be able to program flash memory many 100,000s of times before it starts to fail.
likewise there should be no limiting factors when it comes to the time delay between programming.
i'm guessing from your post that your microcontroller works for a little while but stops after you have programmed it a few times?
in searching for your problem, i would check things like the maximum current you are allowed to draw from your microcontroller's pins. maybe you are sinking too much current.
inductive loads also cause problems when connected straight to microcontroller's pins. (examples of inductive loads are relays, motors and solenoids.) when you switch off an inductive load, current is released, through the microcontroller's pin which can cause damage.
also make sure you have capacitors between your power lines, physically close to the microcontroller to help protect it from spikes in the power supply caused by other components.