Too many eggs in a single basket is always a dangerous strategy, it will work perfectly for a long time and then one day you lose all your eggs. That's only a matter of time.
But we do have examples of such crop failures due to monocultures in 'regular' agriculture. All we have with regards to a GMO problem is speculation and a hope that it will never happen.
The only instance that I'm familiar with that shows a little bit of what the risks are is a south african incident where farmers lost up to 80% of their GMO corn crops.
http://www.dailymail.co.uk/news/worldnews/article-1082559/Th...
http://www.pbs.org/frontlineworld/rough/2005/07/seeds_of_sui...
Usually, if we look only at the ones who are actually available on the market, is to enable the use of mass herbicide or resists specific pests. A lot of them look more motivated by marketing factors to create vendor lock-in.
I see GMOs in food as a temporary escape for monocultures. Ultimately I think we'll need to abandon this practice.