After doing a bit of quick research it's more like 100,000 writes. I didn't see any reference to the number of connections and I've never heard that before.

You could completely rewrite your flash drive once an hour for the next 11 years and you wouldn't reach maximum number of rewrites. Of course that doesn't mean any part in the device can't just go bad (includeing the flash). It is electronics afterall and it's prone to failure.

Hard drives (and flash drives) should be backed up on a regular basis at a frequency dependant on how often your data changes. I have a second hard drive in my PC for the sole purpose of doing a scheduled nightly backup of my primary hard drive to it. The theory being that the chances of both hard drives going bad at the same time are pretty slim. If either goes I still have the other. Hard drives will fail when you least expect it. I'm astounded by the people who never backup their hard drive. I've helped a number of people with their PC who I've had to inform them that, "yes, you've lost all your pictures".