I travel for few months every year to Europe to work from my home country (I work remotely). After reading so many crazy stories, I have adopted few rules: I h

I travel for few months every year to Europe to work from my home country (I work remotely). After reading so many crazy stories, I have adopted few rules: I have SSD drive that I use in States. Once I'm ready to go, I swap it with "empty" drive and fire up the OS just to get some updates on files on it, so it doesn't look like it hasn't been used for a long time. Once in Europe, I put the drive that has more tools and my files I use daily. I also use personal DropBox and the most important files are sync over the net when I login from Europe. As to the phone - my network doesn't work in Europe anyways, so instead of selling/throwing away my perfectly working Iphone5, I use it in Europe and my new phone I leave in states. Moreover I cannot say much about driving to Canada, but I was tempted once with saving $150 on a ticket and flying to Europe through Montreal instead of Chicago. That was horrible mistake. That airport is super disorganized and there is literally no staff to help you. No other information than to research for yourself. Few years ago some guy got teased to death because he was so frustrated and I don't blame him... As of the phone in US, I have jailbroken version with an app that allows me to do a triple-click to shut it down completely. I got used to using this trick when I'm pulled over by LE or entering airports or other places... just in case! I don't think I would ever give out my password without talking to a lawyer first.