That reminds i still have to sort photos from my recent trip. Haven't even loaded them from the laptop to my desktop yet
But you always have the possibility to sort them during the vacation. Like when you're about to sleep, or just don't have anything to do.
External HD's can be found farily cheap at the moment. Just be sure to get one that's big enough.
You can't be the first one, no.
Bwt, which insurance type were you thinking of? One that protects thiefs or just if you e.g. drop your camera? Or both?
And it wouldn't be the worst thing in the world not to have the insurance. You will just have to buy some protective bag, a lock for your gear when it's at home and stuff like that.
And my advice, begin packing a week (or more) before, so that if you forget to pack something, you have a week to pack it.