Don't wait until you want to sell, to create a gameplan. That allows for emotions to play a larger role, and emotional investing usually ends badly. With that being said, don't be afraid to stray from your plan in the future.
Rather than planning on selling all your silver at once, create a plan that allows you to sell off a certain amount at each price point. Keep in mind, you don't need a plan to sell off all your silver. Keeping a percentage as an emergency fund, for retirement, for after a collapse, etc. is a good idea.
Silver shortages could mean that, one day, you're selling even generic silver at a premium.
Waiting for a total collapse of the system? Keep an eye on the world around you, for signs of a deterioration of society, currency, and government.
You should go into this with the mindset of preserving wealth. Profits will likely happen, but those should be an icing on the cake.
Every purchase you make should involve asking yourself whether you can recover the premium, or not.
When you sell your silver, convert that fiat into some other asset of tangible value.
In 2011, some silver pundits advised stackers to no sell. Hindsight is 20/20, but you should make these decisions for yourself.
Even if you're likely to come out ahead in silver, always diversify your investment to some degree. Remember, you can diversify within silver and gold, as well (generic silver, government coins, etc.)
You want to sell your silver at a time of your choosing, not when you're desperate for cash.
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