Bob would like to create a master drive that he can put in a safe deposit box that has all his private information on it. Leo says that's a good idea, but he doesn't really have to go to that extreme. One option is Google Docs, which would be sharable to his attorney.
There's also Database Browser. A simple spreadsheet would also work, and may be best because he would be able to sort by column. If Bob is worried about security, he can password protect the document. Another great free option is Evernote. Bob can use his phone to take pictures or make notes and then upload them directly to it.
Leo also suggests putting some data on his smartphone, like medical information. First responders are trained to look at mobile phones to find important information. It's called "ICE" (In Case of Emergency).